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Volume 68 
Part 1 
Pages o139-o140  
January 2012  

Received 9 December 2011
Accepted 9 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.103
Data-to-parameter ratio = 18.1
Details
Open access

1-[2-(2,4-Dichlorobenzyloxy)-2-(furan-2-yl)ethyl]-1H-benzotriazole

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

In the title compound, C19H15Cl2N3O2, the benzotriazole ring system is approximately planar [maximum deviation = 0.018 (2) Å] and its mean plane is oriented at dihedral angles of 30.70 (5) and 87.38 (4)°, respectively, to the furan and benzene rings while the dihedral angle between furan and benzene rings is 74.46 (6)°. In the crystal, weak C-H...N hydrogen bonds link the molecules into chains along the b axis. [pi]-[pi] stacking interactions between the parallel dichlorobenzene rings of adjacent molecules [centroid-centroid distance = 3.6847 (9) Å] and weak C-H...[pi] interactions 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.]); Özel Güven et al. (2007a[Özel Güven, Ö., Erdogan, T., Göker, H. & Yildiz, S. (2007a). Bioorg. Med. Chem. Lett. 17, 2233-2236.],b[Özel Güven, Ö., Erdogan, T., Göker, H. & Yildiz, S. (2007b). J. Heterocycl. Chem. 44, 731-734.]); Peeters et al. (1979[Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979). Acta Cryst. B35, 2461-2464.]); Freer et al. (1986[Freer, A. A., Pearson, A. & Salole, E. G. (1986). Acta Cryst. C42, 1350-1352.]). For related structures, see: Özel Güven et al. (2008[Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008). Acta Cryst. E64, o1437.], 2009[Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2009). Acta Cryst. E65, o2868-o2869.], 2010a[Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2010a). Acta Cryst. E66, o107-o108.],b[Özel Güven, Ö., Bayraktar, M., Coles, S. J. & Hökelek, T. (2010b). Acta Cryst. E66, o1246-o1247.], 2011[Özel Güven, Ö., Bayraktar, M., Coles, S. J. & Hökelek, T. (2011). Acta Cryst. E67, o3177-o3178.]. For the synthesis of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanol, see: Özel Güven et al. (2012[Özel Güven, Ö., Bayraktar, M., Coles, S. J. & Hökelek, T. (2012). Acta Cryst. E68, o72.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15Cl2N3O2

  • Mr = 388.24

  • Monoclinic, P 21 /c

  • a = 11.5452 (2) Å

  • b = 20.0350 (5) Å

  • c = 8.3317 (2) Å

  • [beta] = 105.598 (2)°

  • V = 1856.21 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 120 K

  • 0.50 × 0.30 × 0.08 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 = 0.837, Tmax = 0.971

  • 31461 measured reflections

  • 4251 independent reflections

  • 3252 reflections with I > 2[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.103

  • S = 1.04

  • 4251 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C14-C19 ring.

D-H...A D-H H...A D...A D-H...A
C4-H4...N3i 0.93 2.59 3.452 (2) 155
C8-H8...Cgii 0.93 2.92 3.782 (2) 155
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y, -z+1.

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: XU5406 ).


Acknowledgements

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

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Freer, A. A., Pearson, A. & Salole, E. G. (1986). Acta Cryst. C42, 1350-1352.  [CrossRef] [details]
Hirokawa, Y., Yamazaki, H., Yoshida, N. & Kato, S. (1998). Bioorg. Med. Chem. Lett. 8, 1973-1978.  [CrossRef] [ChemPort] [PubMed]
Kopanska, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2004). Bioorg. Med. Chem. 12, 2617-2624.  [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. (2010b). Acta Cryst. E66, o1246-o1247.  [CSD] [CrossRef] [details]
Özel Güven, Ö., Bayraktar, M., Coles, S. J. & Hökelek, T. (2011). Acta Cryst. E67, o3177-o3178.  [CrossRef] [details]
Özel Güven, Ö., Bayraktar, M., Coles, S. J. & Hökelek, T. (2012). Acta Cryst. E68, o72.  [CrossRef] [details]
Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008). Acta Cryst. E64, o1437.  [CSD] [CrossRef] [details]
Özel Güven, Ö., Erdogan, T., Göker, H. & Yildiz, S. (2007a). Bioorg. Med. Chem. Lett. 17, 2233-2236.  [PubMed]
Özel Güven, Ö., Erdogan, T., Göker, H. & Yildiz, S. (2007b). J. Heterocycl. Chem. 44, 731-734.
Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2009). Acta Cryst. E65, o2868-o2869.  [CrossRef] [details]
Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2010a). Acta Cryst. E66, o107-o108.  [CSD] [CrossRef] [details]
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979). Acta Cryst. B35, 2461-2464.  [CrossRef] [details] [ISI]
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, o139-o140   [ doi:10.1107/S1600536811053104 ]

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