2-(1H-Benzotriazol-1-yl)-1-(furan-2-yl)ethanol

Özden Özel Güven; Meral Bayraktar; Simon J Coles; Tuncer Hökelek

doi:10.1107/S1600536811051798

. 2011 Dec 10;68(Pt 1):o72. doi: 10.1107/S1600536811051798

2-(1H-Benzotriazol-1-yl)-1-(furan-2-yl)ethanol

Özden Özel Güven ^a, Meral Bayraktar ^a, Simon J Coles ^b, Tuncer Hökelek ^c,^*

PMCID: PMC3254427 PMID: 22259573

Abstract

In the title compound, C₁₂H₁₁N₃O₂, the benzotriazole ring system is approximately planar [maximum deviation = 0.008 (1) Å] and its mean plane is oriented at a dihedral angle of 24.05 (4)° with respect to the furan ring. In the crystal, O—H⋯N hydrogen bonds link the molecules into chains along the ac diagonal. π–π stacking between the furan rings, between the triazole and benzene rings, and between the benzene rings [centroid–centroid distances = 3.724 (1), 3.786 (1) and 3.8623 (9) Å] are also observed.

Related literature

For general background to the biological activity of benzotriazole derivatives, see: Hirokawa et al. (1998 ▶); Yu et al. (2003 ▶); Kopanska et al. (2004 ▶). For related structures, see: Caira et al. (2004 ▶); Katritzky et al. (2001 ▶); Özel Güven et al. (2008 ▶, 2010 ▶, 2011 ▶); Nanjunda Swamy et al. (2006 ▶).

Experimental

Crystal data

C₁₂H₁₁N₃O₂
M _r = 229.24
Monoclinic,
a = 11.3606 (4) Å
b = 11.1034 (4) Å
c = 8.7860 (2) Å
β = 96.938 (2)°
V = 1100.16 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 120 K
0.50 × 0.50 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.953, T _max = 0.981
12372 measured reflections
2531 independent reflections
2166 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.139
S = 1.11
2531 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051798/xu5402sup1.cif

e-68-00o72-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051798/xu5402Isup2.hkl

e-68-00o72-Isup2.hkl^{(121.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811051798/xu5402Isup3.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
O1—H1⋯N3ⁱ	0.82	2.26	2.7968 (18)	123

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Zonguldak Karaelmas University Research Fund (project No. 2010-13-02-05).

supplementary crystallographic information

Comment

Azole compounds have important biological activities. Benzotriazol derivatives also exhibit a good degree of analgesic, anti-inflammatory, diuretic, antiviral and antihypertensive activities (Kopanska et al., 2004; Yu et al., 2003; Hirokawa et al., 1998). Crystal structures of similar compounds like 1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol (Özel Güven et al., 2008), 2-(1H-benzotriazol-1-yl)-1-phenylethanol (Özel Güven et al., 2010), 2-(1H-benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropan-1-ol (Özel Güven et al., 2011), fluconazole (Caira et al., 2004), and other benzotriazole ring possesing compounds (Katritzky et al., 2001; Nanjunda Swamy et al., 2006) have been reported before. Now, we report herein the crystal structure of the title alcohol, (I).

In the molecule of the title compound (Fig. 1), the bond lengths and angles are generally within normal ranges. The planar benzotriazole ring [B (N1-N3/C7-C12)] is oriented with respect to the furan [A (O2/C2-C5)] ring at a dihedral angle of A/B = 24.05 (4)°. Atom C6 is 0.043 (2) Å away from the plane of the benzotriazole ring and atoms C1 and O1 are 0.010 (2) and 0.043 (1) Å away from the plane of the furan ring, respectively.

In the crystal, O—H···N hydrogen bonds (table 1) link the molecules into chains (Fig. 2). There also exist π···π contacts between the furan rings, between the triazole and benzene rings and between the benzene rings, Cg1—Cg1ⁱ, Cg2—Cg3ⁱⁱ and Cg3—Cg3ⁱⁱ, may further stabilize the structure [centroid-centroid distances = 3.724 (1), 3.786 (1) and 3.8623 (9) Å; symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) -x, 1 - y, 1 - z; Cg1, Cg2 and Cg3 are the centroids of the rings A (O2/C2-C5), C (N1-N3/C7/C12) and D (C7-C12), respectively].

Experimental

The title compound, (I), was synthesized by reduction of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanone with sodiumborohydrate. A mixture of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanone (1010 mg, 4.44 mmol) and sodium borohydrate (561 mg, 8.89 mmol) in ethanol (50 ml) was refluxed for 4 h. After evaporation of the solvent, the mixture was neutralized with dilute HCl, and then refluxed for 30 min. After the mixture was cooled, the solution was alkalinized with dilute NaOH and the resulting precipitate was filtered. The filtrate was extracted with chloroform, then the organic phase was dried and evaporated. The residue was crystallized from 2-propanol to obtain colorless crystals suitable for X-ray analysis (yield; 634 mg, 62%).