5-(4-Ethoxy­benzyl)-1H-tetra­zole

Yun-Long Gao; Gui-Long Zhao; Hua Shao; Wei Liu; Jian-wu Wang

doi:10.1107/S1600536809055597

. 2010 Jan 9;66(Pt 2):o322. doi: 10.1107/S1600536809055597

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

Yun-Long Gao ^a, Gui-Long Zhao ^b, Hua Shao ^b, Wei Liu ^a, Jian-wu Wang ^a,^*

PMCID: PMC2979912 PMID: 21579752

Abstract

In the title molecule, C₁₀H₁₂N₄O, the tetrazole and benzene rings form a dihedral angle of 67.52 (2)°. In the crystal, intermolecular N—H⋯N hydrogen bonds link the molecules into chains along the a axis. The relatively short distance of 3.760 (3) Å between the centroids of the tetrazole rings suggests the existence of π–π interactions.

Related literature

For details of the biological activities of sodium-glucose co-transporter 2 (SGLT2) inhibitors, see: Arakawa et al. (2001 ▶); Meng et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₀H₁₂N₄O
M _r = 204.24
Monoclinic,
a = 4.9291 (10) Å
b = 18.145 (4) Å
c = 11.363 (2) Å
β = 99.19 (3)°
V = 1003.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 K
0.34 × 0.06 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T _min = 0.969, T _max = 0.996
6870 measured reflections
1768 independent reflections
1487 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.103
S = 1.10
1768 reflections
142 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: CrystalClear (Rigaku, 2007 ▶); 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/S1600536809055597/cv2684sup1.cif

e-66-0o322-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055597/cv2684Isup2.hkl

e-66-0o322-Isup2.hkl^{(87.1KB, 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
N1—H1⋯N4ⁱ	0.91 (1)	1.90 (1)	2.7897 (16)	166 (1)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Sodium-Glucose Cotransporter 2 (SGLT2) inhibitors constitute a new class of antidiabetic agents (Arakawa et al., 2001; Meng et al., 2008). The title compound, (I), was prepared as an intermediate of a new class of SGLT2 inhibitors designed in our laboratories.

In (I) (Fig. 1), all bond lengths in the molecular are normal (Allen et al., 1987). Atoms O1/C2/C9/C10 lie in the benzene ring (C3—C8) plane with a maximun deviation of 0.045 (2) Å for O1 . The tetrazole ring (N1—N4/C1) forms the dihedral angle of 67.52 (2) ° with the benzene ring (C3—C8).

In the crystal structure, relatively short distance of 3.760 (3) Å between the centroids of tetrazole rings suggests an existence of π—π interactions. Intermolecular N—H···N hydrogen bonds (Table 1) link the molecules related by translation along axis a into chains.

Experimental

A round-bottomed flask was charged with 1.61 g (10 mmol) of 4-ethoxyphenylacetonitrile, 3.25 g (50 mmol) of sodium azide and 2.67 g (50 mmol) of ammonium chloride and 50 ml of DMF, and the resulting mixture was stirred at 120 ° C for 15 h. On complete cooling, the mixture was filtered to remove the existing solid and the filtrate was evaporated on a rotary evaporator equipped with an oil pump, and the residue was dissolved in 100 ml of water. The aqueous solution thus obtained was adjusted to pH = 2 with concentrated hydrochloric acid, when it turned turbid. This turbid mixture was cooled with ice-water bath and stirred for complete crystallization. The precipitated crystals were collected via suction filtration and dried at 60° C in vacuo to afford the title product as white crystals 1.68 g (yield 82.3%). Crystals suitable for single-crystal X-ray diffraction were obtained via slow evaporation at room temperature of a solution of the pure title compound in dichloromethane/petroleum ether.