[Journal logo]

Volume 65 
Part 4 
Page o917  
April 2009  

Received 20 March 2009
Accepted 24 March 2009
Online 28 March 2009

[at2749sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 14.0
Details
Open access

1-(2,3,5,6-Tetramethylbenzyloxy)-1H-benzotriazole

B. Ravindran Durai Nayagam,a* Samuel Robinson Jebas,b J. P Edward Rajkumarc and Dieter Schollmeyerd

aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India,bDepartment of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India,cDepartment of Physics, Popes College, Sawyerpuram 628 251, Tamilnadu, India, and dInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: b_ravidurai@yahoo.com

In the title compound, C17H19N3O, the benzotriazole ring is essentially planar, with a maximum deviation of 0.0069 (15) Å. The mean plane of the benzotriazole ring forms a dihedral angle of 13.16 (4)° with the mean plane of the benzene ring. The crystal packing is stabilized by [pi]-[pi] stacking interactions, with a centroid-centroid distance of 3.8077 (12) Å, together with weak C-H...[pi] interactions. Molecules are stacked along the a axis.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the biological activity of N-oxide and benzotriazole derivatives, see: Katarzyna et al. (2005[Katarzyna, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2005). Bioorg Med. Chem. 13, 3601-3616.]); Sarala et al. (2007[Sarala, G., Swamy, S. N., Prabhuswamy, B., Andalwar, S. M., Prasad, J. S. & Rangappa, K. S. (2007). Anal. Sci. 23, 25-26.]). For applications of benzotriazole, see: Kopec et al. (2008[Kopec, E. A., Zwolska, Z. & Kazimierczuk, A. O. Z. (2008). Acta Pol. Pharm. Drug Res. 65, 435-439.]); Krawczyk & Gdaniec (2005[Krawczyk, S. & Gdaniec, M. (2005). Acta Cryst. E61, o2967-o2969.]); Smith et al. (2001[Smith, G., Bottle, S. E., Reid, D. A., Schweinsberg, D. P. & Bott, R. C. (2001). Acta Cryst. E57, o531-o532.]); Sha et al. (1996[Sha, G., Wang, W. & Ren, T. (1996). Mocha Xuebao, 16, 344-350.]). For 1-hydroxybenzotriazole, see: Anderson et al. (1963[Anderson, G. W., Zimmerman, J. E. & Calahan, F. M. (1963). J. Am. Chem. Soc. 85, 3039-3039.]); Bosch et al. (1983[Bosch, R., Jung, G. & Winter, W. (1983). Acta Cryst. C39, 1089-1092.]).

[Scheme 1]

Experimental

Crystal data

  • C17H19N3O

  • Mr = 281.35

  • Monoclinic, P 21 /c

  • a = 4.9737 (8) Å

  • b = 26.3838 (18) Å

  • c = 11.490 (2) Å

  • [beta] = 105.977 (7)°

  • V = 1449.5 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.65 mm-1

  • T = 193 K

  • 0.51 × 0.51 × 0.45 mm
Data collection

  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (CORINC; Draeger & Gattow, 1971[Draeger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]) Tmin = 0.731, Tmax = 0.759

  • 2861 measured reflections

  • 2729 independent reflections

  • 2578 reflections with I > 2[sigma](I)

  • Rint = 0.050

  • 3 standard reflections frequency: 60 min intensity decay: 1%
Refinement

  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.135

  • S = 1.08

  • 2729 reflections

  • 195 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18C...Cg3i 0.98 2.85 3.6701 (18) 141
C20-H20B...Cg3ii 0.98 2.80 3.682 (2) 150
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z. Cg3 is the centroid of the C12-C17 ring.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: CORINC (Draeger & Gattow, 1971[Draeger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL 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: AT2749 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Anderson, G. W., Zimmerman, J. E. & Calahan, F. M. (1963). J. Am. Chem. Soc. 85, 3039-3039.  [CrossRef] [ChemPort] [ISI]
Bosch, R., Jung, G. & Winter, W. (1983). Acta Cryst. C39, 1089-1092.  [CrossRef] [details]
Draeger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761-762.  [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Katarzyna, K., Najda, A., Zebrowska, J., Chomicz, L., Piekarczyk, J., Myjak, P. & Bretner, M. (2005). Bioorg Med. Chem. 13, 3601-3616.
Kopec, E. A., Zwolska, Z. & Kazimierczuk, A. O. Z. (2008). Acta Pol. Pharm. Drug Res. 65, 435-439.
Krawczyk, S. & Gdaniec, M. (2005). Acta Cryst. E61, o2967-o2969.  [CSD] [CrossRef] [details]
Sarala, G., Swamy, S. N., Prabhuswamy, B., Andalwar, S. M., Prasad, J. S. & Rangappa, K. S. (2007). Anal. Sci. 23, 25-26.  [PubMed]
Sha, G., Wang, W. & Ren, T. (1996). Mocha Xuebao, 16, 344-350.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Bottle, S. E., Reid, D. A., Schweinsberg, D. P. & Bott, R. C. (2001). Acta Cryst. E57, o531-o532.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2009). E65, o917  [ doi:10.1107/S1600536809010794 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.