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Volume 69 
Part 2 
Page o247  
February 2013  

Received 3 January 2013
Accepted 8 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.068
wR = 0.217
Data-to-parameter ratio = 13.5
Details
Open access

4-(1-Methylethyl)-N-((E)-4-{[1-(prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzylidene)aniline

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: akkurt@erciyes.edu.tr, dmntahir_uos@yahoo.com

In the title compound, C22H24N4O, the terminal and central benzene rings make dihedral angles of 52.7 (3) and 43.8 (2)°, respectively, with the triazole ring. The dihedral angle between the benzene rings is 8.9 (2)°. The crystal structure features C-H...[pi] interactions. The atoms of the terminal propenyl group are disordered over two sets of sites, with a refined occupancy ratio of 0.714 (14):0.286 (14).

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 general background to the properties of Schiff bases, see: Ajello & Cusmanos (1940[Ajello, T. & Cusmanos, G. (1940). Chim. Ital. 70, 770-778.]); Dhar & Taploo (1982[Dhar, D. N. & Taploo, C. L. (1982). J. Sci. Ind. Res. 41, 501-506.]); Holla et al. (2005[Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Poojary, B., Akberali, P. M. & Kumari, N. S. (2005). Eur. J. Med. Chem. 40, 1173-1178.]); Singh et al. (2012[Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M. S., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594-600.]); Supuran et al. (1996[Supuran, C. T., Barboiu, M., Luca, C., Pop, E., Brewster, M. E. & Dinculescu, A. (1996). Eur. J. Med. Chem. 31, 597-606.]).

[Scheme 1]

Experimental

Crystal data
  • C22H24N4O

  • Mr = 360.45

  • Monoclinic, P 21 /c

  • a = 5.5885 (11) Å

  • b = 8.3929 (18) Å

  • c = 42.069 (9) Å

  • [beta] = 92.149 (10)°

  • V = 1971.8 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.18 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.982, Tmax = 0.986

  • 13866 measured reflections

  • 3451 independent reflections

  • 1259 reflections with I > 2[sigma](I)

  • Rint = 0.082

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.217

  • S = 0.96

  • 3451 reflections

  • 256 parameters

  • 7 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the N2-N4/C18/C19 1H-1,2,3-triazole and C11-C16 benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg3i 0.93 2.96 3.752 (5) 144
C8-H8A...Cg1ii 0.96 2.80 3.678 (6) 153
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2382 ).


Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Ajello, T. & Cusmanos, G. (1940). Chim. Ital. 70, 770-778.  [ChemPort]
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.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dhar, D. N. & Taploo, C. L. (1982). J. Sci. Ind. Res. 41, 501-506.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Poojary, B., Akberali, P. M. & Kumari, N. S. (2005). Eur. J. Med. Chem. 40, 1173-1178.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M. S., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594-600.  [ISI] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Supuran, C. T., Barboiu, M., Luca, C., Pop, E., Brewster, M. E. & Dinculescu, A. (1996). Eur. J. Med. Chem. 31, 597-606.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2013). E69, o247  [ doi:10.1107/S1600536813000755 ]

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