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Volume 68 
Part 1 
Page o72  
January 2012  

Received 30 November 2011
Accepted 1 December 2011
Online 10 December 2011

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Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.054
wR = 0.139
Data-to-parameter ratio = 16.3
Details
Open access

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

Özden Özel Güven,a Meral Bayraktar,a Simon J. Colesb and Tuncer Hökelekc*

aDepartment of Chemistry, Zonguldak Karaelmas University, 67100 Zonguldak, Turkey,bDepartment of Chemistry, Southampton University, Southampton SO17 1BJ, England, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

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. [pi]-[pi] 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[Hirokawa, Y., Yamazaki, H., Yoshida, N. & Kato, S. (1998). Bioorg. & Med. Chem. Lett. 8, 1973-1978.]); Yu et al. (2003[Yu, K. L., Zhang, Y., Civiello, R. L., Kadow, K. F., Cianci, C., Krystal, M. & Meanwell, N. A. (2003). Bioorg. Med. Chem. Lett. 13, 2141-2144.]); Kopanska et al. (2004[Kopanska, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2004). Bioorg. Med. Chem. 12, 2617-2624.]). For related structures, see: Caira et al. (2004[Caira, M. R., Alkhamis, K. A. & Obaidat, R. M. (2004). J. Pharm. Sci. 93, 601-611.]); Katritzky et al. (2001[Katritzky, A. R., Zhang, S. M., Kurz, T., Wang, M. Y. & Steel, P. J. (2001). Org. Lett. 3, 2807-2809.]); Özel Güven et al. (2008[Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2008). Acta Cryst. E64, o1254.], 2010[Özel Güven, Ö., Bayraktar, M., Coles, S. J. & Hökelek, T. (2010). Acta Cryst. E66, o959.], 2011[Özel Güven, Ö., Çapanlar, S., Coles, S. J. & Hökelek, T. (2011). Acta Cryst. E67, o2510.]); Nanjunda Swamy et al. (2006[Nanjunda Swamy, S., Basappa, Sarala, G., Priya, B. S., Gaonkar, S. L., Shashidhara Prasad, J. & Rangappa, K. S. (2006). Bioorg. Med. Chem. Lett. 16, 999-1004.]).

[Scheme 1]

Experimental

Crystal data

  • C12H11N3O2

  • Mr = 229.24

  • Monoclinic, P 21 /c

  • a = 11.3606 (4) Å

  • b = 11.1034 (4) Å

  • c = 8.7860 (2) Å

  • [beta] = 96.938 (2)°

  • V = 1100.16 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.981

  • 12372 measured reflections

  • 2531 independent reflections

  • 2166 reflections with I > 2[sigma](I)

  • Rint = 0.037
Refinement

  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.139

  • S = 1.11

  • 2531 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

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
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5402 ).

Acknowledgements

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

References

Caira, M. R., Alkhamis, K. A. & Obaidat, R. M. (2004). J. Pharm. Sci. 93, 601-611.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hirokawa, Y., Yamazaki, H., Yoshida, N. & Kato, S. (1998). Bioorg. & Med. Chem. Lett. 8, 1973-1978.  [CrossRef] [ChemPort]
Katritzky, A. R., Zhang, S. M., Kurz, T., Wang, M. Y. & Steel, P. J. (2001). Org. Lett. 3, 2807-2809.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kopanska, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2004). Bioorg. Med. Chem. 12, 2617-2624.  [CrossRef] [PubMed] [ChemPort]
Nanjunda Swamy, S., Basappa, Sarala, G., Priya, B. S., Gaonkar, S. L., Shashidhara Prasad, J. & Rangappa, K. S. (2006). Bioorg. Med. Chem. Lett. 16, 999-1004.  [CSD] [CrossRef] [PubMed] [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Özel Güven, Ö., Bayraktar, M., Coles, S. J. & Hökelek, T. (2010). Acta Cryst. E66, o959.  [CrossRef] [details]
Özel Güven, Ö., Çapanlar, S., Coles, S. J. & Hökelek, T. (2011). Acta Cryst. E67, o2510.  [CSD] [CrossRef] [details]
Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2008). Acta Cryst. E64, o1254.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yu, K. L., Zhang, Y., Civiello, R. L., Kadow, K. F., Cianci, C., Krystal, M. & Meanwell, N. A. (2003). Bioorg. Med. Chem. Lett. 13, 2141-2144.  [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2012). E68, o72  [ doi:10.1107/S1600536811051798 ]

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