5-(4-Chloro­benz­yl)-1H-tetra­zole

Pei-Jiang Liu; Dong-Sheng Ma; Shuai Zhang; Guang-Feng Hou

doi:10.1107/S1600536811028388

. 2011 Jul 23;67(Pt 8):o2088. doi: 10.1107/S1600536811028388

5-(4-Chlorobenzyl)-1H-tetrazole

Pei-Jiang Liu ^a, Dong-Sheng Ma ^a,^*, Shuai Zhang ^a, Guang-Feng Hou ^a

PMCID: PMC3213529 PMID: 22091108

Abstract

In the title compound, C₈H₇ClN₄, the phenyl and tetrazole rings are inclined at a dihedral angle of 67.52 (6)°. In the crystal, molecules are linked by an N—H⋯N hydrogen bond into a chain structure along [010]. π–π interactions with centroid–centroid distances of 3.526 (1) Å between adjacent tetrazole rings further link the chains, forming a ribbon structure.

Related literature

For background to tetrazole compounds, see: Kitagawa et al. (2004 ▶); Zhao et al. (2008 ▶); For the synthesis, see: Luo et al. (2006 ▶).

Experimental

Crystal data

C₈H₇ClN₄
M _r = 194.63
Monoclinic,
a = 14.654 (3) Å
b = 4.9321 (10) Å
c = 12.688 (3) Å
β = 105.63 (3)°
V = 883.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 293 K
0.40 × 0.38 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.860, T _max = 0.944
8039 measured reflections
2015 independent reflections
1546 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.094
S = 1.08
2015 reflections
122 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002) ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028388/ng5199sup1.cif

e-67-o2088-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028388/ng5199Isup2.hkl

e-67-o2088-Isup2.hkl^{(99.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811028388/ng5199Isup3.cml

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
N4—H1⋯N1ⁱ	0.90 (1)	1.92 (1)	2.8013 (15)	168 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Heilongjiang University for supporting this work.

supplementary crystallographic information

Comment

The tetrazole has attracted considerable interesting owing to their structural characterization in coordination chemistry and the extensively application in medicinal chemistry and materials science (Zhao et al. 2008; Kitagawa et al. 2004). Here, we report the synthesis and crystal structure of the title compound.

As shown in fig.1, the benzenyl plane and tetrazole rings form a dihedral angle about 67.52 (6) ° (Fig. 1). In the crystal packing, the molecules are linked by N—H···N hydrogen bonds into a chain structure alone [010] (Fig. 2, Table 1). The π—π interactions with distances of 3.526 (1) Å (center to center) between the adjacent tetrazole rings further link them to form ribbon structure (Fig. 3).

Experimental

The title compound was prepared as follows (Luo et al. 2006):2-(4-chlorophenyl)acetonitrile (6.06 g, 0.04 mol), NaN3 (3.9 g, 0.06 mol) and NH₄Cl (3.21 g, 0.06 mol) were dissolved in DMF (120 ml). The mixture was reflux for 20 h under stirring. Then, it was cooled to room temperature and the mixture was filtered. The solvent was evaporated and the residue was poured into cold water (30 ml) to give the title compound (4.32 g, 55.5 %). The crystals suitable for X-ray diffraction were obtained from 10 mL mixed solution of ethanol and water (1:1).