(E)-2-[(2-Formyl­phen­oxy)meth­yl]-3-(4-methyl­phen­yl)prop-2-ene­nitrile

Manikandan, N.; Murugavel, S.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536811051415

Volume 68
Part 1
Page o28
January 2012

Received 17 November 2011
Accepted 29 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.133
Data-to-parameter ratio = 17.4
Details

(E)-2-[(2-Formylphenoxy)methyl]-3-(4-methylphenyl)prop-2-enenitrile

N. Manikandan,^a S. Murugavel,^b ^* D. Kannan ^c and M. Bakthadoss ^c

^aDepartment of Physics, Bharathidasan Engineering College, Nattrampalli, Vellore 635 854, India,^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^cDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C₁₈H₁₅NO₂, the dihedral angle between the two benzene rings is 74.8 (1)°. The carbonitrile chain is almost linear, the C-C-N angle being 176.2 (2)°. In the crystal, [pi] - [pi] interactions [centroid-centroid distance = 3.842 (1) Å] are observed.

Related literature

For background to the synthetic procedure, see: Bakthadoss & Murugan (2010). For related structures, see: Swaminathan et al. (2011); Prasanna et al. (2011).

Experimental

Crystal data

C₁₈H₁₅NO₂
M_r = 277.31
Monoclinic, P 2₁ /c
a = 7.0792 (4) Å
b = 13.7006 (7) Å
c = 15.3587 (9) Å
= 96.782 (2)°
V = 1479.21 (14) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.982, T_max = 0.988
15027 measured reflections
3321 independent reflections
1950 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.133
S = 1.01
3321 reflections
191 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.14 e Å^-3

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia (1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2342 ).

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bakthadoss, M. & Murugan, G. (2010). Eur. J. Org. Chem. pp. 5825-5830.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Prasanna, C. M. S., Sethusankar, K., Rajesh, R. & Raghunathan, R. (2011). Acta Cryst. E67, o2176.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o2000.

organic compounds