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

Özel Güven, Ö.; Bayraktar, M.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536811053104

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 (C-C) = 0.002 Å
R = 0.040
wR = 0.103
Data-to-parameter ratio = 18.1
Details

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

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

^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-HN 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); Yu et al. (2003); Kopanska et al. (2004); Özel Güven et al. (2007a,b); Peeters et al. (1979); Freer et al. (1986). For related structures, see: Özel Güven et al. (2008, 2009, 2010a,b, 2011. For the synthesis of 2-(1H-benzotriazol-1-yl)-1-(furan-2-yl)ethanol, see: Özel Güven et al. (2012).

Experimental

Crystal data

C₁₉H₁₅Cl₂N₃O₂
M_r = 388.24
Monoclinic, P 2₁ /c
a = 11.5452 (2) Å
b = 20.0350 (5) Å
c = 8.3317 (2) Å
= 105.598 (2)°
V = 1856.21 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.837, T_max = 0.971
31461 measured reflections
4251 independent reflections
3252 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.103
S = 1.04
4251 reflections
235 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C14-C19 ring.

D-HA	D-H	HA	DA	D-HA
C4-H4N3ⁱ	0.93	2.59	3.452 (2)	155
C8-H8Cgⁱⁱ	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); 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 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

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organic compounds