1-(4-Chloro­phen­yl)-1H-1,2,3,4-tetra­zole

Jong Tae Kim; D Gayathri; Vivek K Gupta; Rajni Kant; Yeon Tae Jeong

doi:10.1107/S1600536812014353

. 2012 Apr 13;68(Pt 5):o1344. doi: 10.1107/S1600536812014353

1-(4-Chlorophenyl)-1H-1,2,3,4-tetrazole

Jong Tae Kim ^a, D Gayathri ^b, Vivek K Gupta ^c, Rajni Kant ^c, Yeon Tae Jeong ^a,^*

PMCID: PMC3344479 PMID: 22590241

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₇H₅ClN₄, in which the tetrazole and benzene rings are twisted by dihedral angles of 12.9 (1) and 39.8 (1)°. In the crystal, the independent molecules are connected into a tetramer by C—H⋯N hydrogen bonds, generating an R ₄ ⁴(12) graph-set motif.

Related literature

For applications of tetrazoles in medicinal and synthetic chemistry, see: Butler (1996 ▶). For related structures, see: Baek et al. (2012 ▶); Matsunaga et al. (1999 ▶); Lyakhov et al. (2000 ▶, 2001 ▶). For the synthesis, see: Aridoss & Laali (2011 ▶).

Experimental

Crystal data

C₇H₅ClN₄
M _r = 180.60
Monoclinic,
a = 3.8626 (2) Å
b = 27.9946 (10) Å
c = 14.4943 (5) Å
β = 95.640 (3)°
V = 1559.71 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.795, T _max = 0.917
16702 measured reflections
3366 independent reflections
2610 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.101
S = 1.07
3366 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812014353/is5104sup1.cif

e-68-o1344-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014353/is5104Isup2.hkl

e-68-o1344-Isup2.hkl^{(161.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812014353/is5104Isup3.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
C1A—H1A⋯N1Bⁱ	0.93	2.54	3.454 (3)	167
C1B—H1B⋯N1Aⁱⁱ	0.93	2.50	3.406 (3)	163

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

YTJ is thankful for the support provided by the second stage of the BK-21 program. The authors thank the Director, USIC University of Jammu, Jammu Tawi, India, for the X-ray data collection.

supplementary crystallographic information

Comment

Heterocycles in general received much importance in recent years. Tetrazoles represent a unique class of heterocyclic compounds that exhibit a broad range of application both in medicinal and synthetic chemistry (Butler, 1996).

The title compound crystallizes in a monoclinic crystal system with two independent molecules in the asymmetric unit. Bond lengths and angles are comparable with the similar crystal structures (Baek et al., 2012; Lyakhov et al., 2000, 2001; Matsunaga et al., 1999). The tetrazole and benzene rings are planar but not coplanar with the dihedral angle being 12.9 (1) and 39.8 (1)°, respectively, for molecules A and B. Torsion angles C1A—N4A—C2A—C3A [165.7 (2)°] and C1B—N4B—C2B—C3B [-138.5 (3)°] indicate for the difference in the dihedral angle between the two rings in molecules A and B. The chlorine atoms in molecules A and B deviate 0.021 (3) and 0.009 (3) Å, respectively, from the benzene plane. The crystal packing is stabilized by C—H···N intermolecular interactions (Table 1), wherein atom C1 acts as donor to N1 generating an R₄⁴(12) graph-set motif.

Experimental

The title compound was synthesized from the known procedure (Aridoss & Laali, 2011). Fine white diffraction quality crystals were obtained by slow evaporation of its ethanol solution.