5-(1H-Tetra­zol-5-yl)-1H-indole monohydrate

Xing-Wei Cai; Hong-Fei Lu; Zhen Zhou

doi:10.1107/S1600536811018575

. 2011 May 28;67(Pt 6):o1554. doi: 10.1107/S1600536811018575

5-(1H-Tetrazol-5-yl)-1H-indole monohydrate

Xing-Wei Cai ^a,^*, Hong-Fei Lu ^a, Zhen Zhou ^b

PMCID: PMC3120397 PMID: 21754912

Abstract

In the title compound, C₉H₇N₅·H₂O, the interplanar angles between the benzene and tetrazole rings and between the benzene and imidazole rings are 8.71 (3) and 1.32 (2)°, respectively. In the crystal, strong N—H⋯N hydrogen bonds link the organic 5-(1H-tetrazol-5-yl)-1H-indole molecules into chains extended along the b axis. The chains are further interconnected into layers parallel to (100) via strong O—H⋯N and N—H⋯O hydrogen bonds. Furthermore, the layers are interconnected via strong O—H⋯N hydrogen bonds. Moreover, cohesion between the layers is provided by the π–π interactions between the imidazole, tetrazole and benzene rings with centroid–centroid distances of 3.766 (2), 3.832 (2) and 3.733 (2) Å.

Related literature

For applications of tetrazole derivatives, see: Jin et al. (1994 ▶); Fu et al. (2009 ▶). For their use in the synthesis of metal-organic frameworks, see: Brewis et al. (2003 ▶). For related structures, see: Zhao et al. (2008 ▶); Fu et al. (2009 ▶). For the classification of hydrogen bonds, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C₉H₇N₅·H₂O
M _r = 203.21
Orthorhombic,
a = 6.8978 (14) Å
b = 9.953 (2) Å
c = 13.713 (3) Å
V = 941.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.89, T _max = 0.95
9741 measured reflections
1258 independent reflections
971 reflections with I > 2σ(I)
R _int = 0.069

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.105
S = 1.06
1258 reflections
148 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018575/fb2235sup1.cif

e-67-o1554-sup1.cif^{(14.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018575/fb2235Isup2.hkl

e-67-o1554-Isup2.hkl^{(62.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018575/fb2235Isup3.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
N1—H1⋯N3ⁱ	0.87 (3)	2.18 (3)	3.042 (3)	171 (3)
O1W—H1WA⋯N2ⁱⁱ	0.80 (2)	2.08 (2)	2.869 (3)	173 (3)
O1W—H1WB⋯N4ⁱⁱⁱ	0.79 (2)	2.33 (2)	3.098 (3)	164 (3)
N5—H5⋯O1W	0.91 (3)	1.85 (3)	2.757 (3)	173 (3)

Open in a new tab

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

Acknowledgments

This work was supported by a start-up grant from Jiangsu University of Science and Technology, China.

supplementary crystallographic information

Comment

The tetrazole functional derivatives have found a wide range of applications in coordination chemistry as ligands (Fu et al., 2009), in medicinal chemistry as metabolically stable surrogates for the carboxylic acid group (Fu et al., 2009) and in materials science as highly energetical materials for production of tetrazole explosives (Jin et al., 1994). For the varying ability of the tetrazoles to coordinate metal ions, a large number of novel metal-organic frameworks have been synthesized (Brewis et al., 2003). As extension of these works, we report here the crystal structure of the title compound, 5-(1H-tetrazol-5-yl)-1H-indole hydrate.

The interplanar angles between the benzene and the tetrazole and the benzene and imidazole rings equal to 8.71 (3)° and 1.32 (2)°, respectively. The geometric parameters of the tetrazole ring are comparable to those in the related molecules (Zhao et al., 2008; Fu et al., 2009).

The molecular packing is stabilized by strong intermolecular N—H···O, N—H···N and O—H···N hydrogen bonds (the classification of the hydrogen bonds is according to Desiraju & Steiner, 1999). The H-bonds link the molecules into a three-dimensional network (Fig. 2 and Tab. 1). In a more detail, N1-H1···N3 connects the molecules into chains extended along the b-axis. These chains are interconnected by the hydrogen bonds O1W—H1WA···N2 and N5—H5···O1W, forming thus layers parallel to (1 0 0) - see Fig. 2 and Tab. 1. The hydrogen bond O1W—H1WB···N4 interconnects the layers.

The layers are also connected by the π-electron ring··· π-electron ring interactions. The centroid—centroid distances are Cg1—Cg2 (1 + x, y, z) = 3.766 (2) Å; Cg1—Cg2 (1/2 + x, 3/2 - y, 1 - z) = 3.832 (2)Å and Cg3—Cg3 (1/2 + x, 3/2 - y or -1/2 + x, 3/2 - y, 1 - z) = 3.733 (2) Å , where Cg1, Cg2 and Cg3 are the centroids referring to the imidazole, tetrazole and the benzene rings, respectively.

Experimental

5-(1H-tetrazol-5-yl)-1H-indole was obtained commercially from Alfa Aesar. Colourless block-shaped crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol/water (2:1 v/v) solution.