4-[4-(1H-Tetra­zol-5-yl)phen­oxy]benzaldehyde

Jing Lu; Jiao Xu; Li-Wei Ni; Wei-Li Ma; Zhen-Ting Du

doi:10.1107/S1600536811044254

. 2011 Oct 29;67(Pt 11):o3106. doi: 10.1107/S1600536811044254

4-[4-(1H-Tetrazol-5-yl)phenoxy]benzaldehyde

Jing Lu ^a, Jiao Xu ^a, Li-Wei Ni ^a, Wei-Li Ma ^a, Zhen-Ting Du ^a,^*

PMCID: PMC3247491 PMID: 22220109

Abstract

The asymmetric unit of the title compound, C₁₄H₁₀N₄O₂, contains two independent molecules with similar structures. In one molecule, the tetrazole ring is oriented at dihedral angles of 17.71 (16) and 57.13 (17)°, respectively, to the central benzene ring and the terminal benzene ring; in the other molecule, the corresponding dihedral angles are 16.46 (18) and 75.87 (18)°. Intermolecular N—H⋯N hydrogen bonds and weak C—H⋯O and C—H⋯N hydrogen bonds occur in the crystal structure.

Related literature

For the synthesis of 5-substituted 1H-tetrazoles, see: Ostrovskii et al. (2008 ▶); Saikia & Phukan (2009 ▶); Nasrollahzadeh et al. (2009 ▶); Teimouri & Najafi Chermahini (2011 ▶). For related structures, see: Li et al. (2008 ▶); Hu et al. (2009 ▶); Xu et al. (2010 ▶); Deng et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₁₀N₄O₂
M _r = 266.26
Triclinic,
a = 9.854 (4) Å
b = 9.948 (4) Å
c = 14.139 (6) Å
α = 98.537 (4)°
β = 106.668 (4)°
γ = 99.737 (4)°
V = 1279.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
9274 measured reflections
4683 independent reflections
2623 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.142
S = 1.01
4683 reflections
369 parameters
30 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I, New_Global_Publ_Block. DOI: 10.1107/S1600536811044254/xu5357sup1.cif

e-67-o3106-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044254/xu5357Isup2.hkl

e-67-o3106-Isup2.hkl^{(229.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811044254/xu5357Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811044254/xu5357Isup4.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—H1N⋯N8ⁱ	0.91 (3)	1.94 (3)	2.849 (4)	174 (2)
N5—H2N⋯N4ⁱⁱ	0.90 (3)	2.03 (3)	2.924 (3)	176 (3)
C4—H4⋯O4	0.93	2.54	3.420 (4)	158
C17—H17⋯N3ⁱⁱ	0.93	2.58	3.365 (4)	143
C23—H23⋯O2ⁱⁱⁱ	0.93	2.42	3.262 (6)	151

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

Acknowledgments

Financial support from the Fundamental Research Funds for the Central Universities in NWSUAF (No. QN2009048) and the opening project of Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin (BRTD1004) as well as the National Natural Science Foundation of China (20802058) are greatly appreciated.

supplementary crystallographic information

Comment

Tetrazoles play a variety of roles in coordination chemistry, medicinal chemistry, materials chemistry etc. (Ostrovskii et al., 2008). We intended to find a new way for preparation of tetrazoles using a new solid acid which is regarded as a green catalyst. In order to confirm the verity of the final product, the single crystal X-ray analysis was performed and the structure is reported here.

Compared with the other phenyltetrazole coplanar structures reported by Li et al. (2008) and Xu et al. (2010), there is torsion between tetrazole rings and neighboring phenyl rings, with a dihedral angle 17.7 (1)° and 16.4 (4)°, respectively.

Experimental

A solution of 4-(4-formylphenoxy)benzonitrile (892 mg, 4 mmol) and sodium azide (780 mg, 12 mmol) in dry DMF (15 mL) at the presence of sulfuric acid on silica gel (5% load, 400 mg ) was heated to 80°C. When the reaction was completed, the solid acid was filtered, 2 mL water was added to the filtration, and then was extracted with ethyl acetate (20 mL × 3). The ethyl acetate layers were combined and washed by 20 mL water, and then 15 mL saturated sodium chloride and dried over anhydrous sodium sulfate. The solution was evaporated and the residue was separated on silica gel column chromatography with a gradient of petroleum ether and ethyl acetate as eluent to yield 570 mg the title compound. The compound was then dissolved in methanol, and colorless crystals were formed on slow evaporation at room temperature over one week.