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Volume 69 
Part 8 
Page o1354  
August 2013  

Received 13 July 2013
Accepted 24 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.056
wR = 0.179
Data-to-parameter ratio = 15.3
Details
Open access

(E)-2-[(2-Formylphenoxy)methyl]-3-(4-isopropylphenyl)acrylonitrile

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India,bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,cDepartment of Organic Chemistry, University of Madras, Guindy campus, Chennai 600 025, India,dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203, Tamil Nadu, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

In the title compound, C20H19NO2, the dihedral angle between the benzene rings is 77.12 (8)°. The terminal isopropyl group is disordered over two orientations, with site occupancies of 0.720 (14) and 0.280 (14). In the crystal, molecules are linked through a weak C-H...O interaction, forming a zigzag chain along the c-axis direction.

Related literature

For the biological activity of cyanoacrylates, see: Zhang et al. (2009[Zhang, D., Zhang, X. & Guo, L. (2009). Acta Cryst. E65, o90.]); Obniska et al. (2005[Obniska, J., Jurczyk, S., Zejc, A., Kaminski, K., Tatarczynska, E. & Stachowicz, K. (2005). Pharmacol. Rep. 57, 170-175.]). For related structures, see: Ye et al. (2009[Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.]); Suresh et al. (2012[Suresh, G., Sabari, V., Srinivasan, J., Mannickam, B. & Aravindhan, S. (2012). Acta Cryst. E68, o570.]); Govindan et al. (2012[Govindan, E., Srinivasan, J., Bakthadoss, M. & SubbiahPandi, A. (2012). Acta Cryst. E68, o484.]).

[Scheme 1]

Experimental

Crystal data
  • C20H19NO2

  • Mr = 305.36

  • Monoclinic, P 21 /c

  • a = 13.3276 (9) Å

  • b = 11.6435 (7) Å

  • c = 11.9965 (9) Å

  • [beta] = 111.800 (3)°

  • V = 1728.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.977, Tmax = 0.985

  • 16125 measured reflections

  • 3532 independent reflections

  • 2004 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.179

  • S = 1.09

  • 3532 reflections

  • 231 parameters

  • 12 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O2i 0.93 2.41 3.236 (3) 149
Symmetry code: (i) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5291 ).


References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Govindan, E., Srinivasan, J., Bakthadoss, M. & SubbiahPandi, A. (2012). Acta Cryst. E68, o484.  [CrossRef] [IUCr Journals]
Obniska, J., Jurczyk, S., Zejc, A., Kaminski, K., Tatarczynska, E. & Stachowicz, K. (2005). Pharmacol. Rep. 57, 170-175.  [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Suresh, G., Sabari, V., Srinivasan, J., Mannickam, B. & Aravindhan, S. (2012). Acta Cryst. E68, o570.  [CSD] [CrossRef] [IUCr Journals]
Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.  [CSD] [CrossRef] [IUCr Journals]
Zhang, D., Zhang, X. & Guo, L. (2009). Acta Cryst. E65, o90.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1354  [ doi:10.1107/S1600536813020618 ]

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