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

Akkurt, M.; Jarrahpour, A.; Chermahini, M.M.; Shiri, P.; Tahir, M.N.

doi:10.1107/S1600536813000755

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 (C-C) = 0.007 Å
Disorder in main residue
R = 0.068
wR = 0.217
Data-to-parameter ratio = 13.5
Details

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

Mehmet Akkurt,^a ^* Aliasghar Jarrahpour,^b Mehdi Mohammadi Chermahini,^b Pezhman Shiri ^b and Muhammad Nawaz Tahir ^c ^*

^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). For general background to the properties of Schiff bases, see: Ajello & Cusmanos (1940); Dhar & Taploo (1982); Holla et al. (2005); Singh et al. (2012); Supuran et al. (1996).

Experimental

Crystal data

C₂₂H₂₄N₄O
M_r = 360.45
Monoclinic, P 2₁ /c
a = 5.5885 (11) Å
b = 8.3929 (18) Å
c = 42.069 (9) Å
= 92.149 (10)°
V = 1971.8 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.982, T_max = 0.986
13866 measured reflections
3451 independent reflections
1259 reflections with I > 2(I)
R_int = 0.082

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.217
S = 0.96
3451 reflections
256 parameters
7 restraints
H-atom parameters constrained
_max = 0.20 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C2-H2Cg3ⁱ	0.93	2.96	3.752 (5)	144
C8-H8ACg1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) 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.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Poojary, B., Akberali, P. M. & Kumari, N. S. (2005). Eur. J. Med. Chem. 40, 1173-1178.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Supuran, C. T., Barboiu, M., Luca, C., Pop, E., Brewster, M. E. & Dinculescu, A. (1996). Eur. J. Med. Chem. 31, 597-606.

organic compounds