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Volume 68 
Part 1 
Page o229  
January 2012  

Received 3 December 2011
Accepted 17 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.137
Data-to-parameter ratio = 19.2
Details
Open access

(E)-Methyl 2-[(2-formyl-6-methoxyphenoxy)methyl]-3-phenylacrylate

aPost Graduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: seshadri_pr@yahoo.com

The title compound, C19H18O5, crystallizes with two independent molecules (A and B) in an asymmetric unit in both of which the two aromatic rings are in a bisectional orientation as evidenced by the dihedral angle between them [41.7 (1)° in molecule A and 35.6 (1)° in molecule B]. Both molecules adopt an E configuration with respect to the C=C bond. An intramolecular C-H...O hydrogen-bond occurs in molecule A. The crystal packing features intermolecular C-H...O interactions.

Related literature

For background to the synthesis, see: Bakthadoss et al. (2009[Bakthadoss, M., Sivakumar, G. & Kannan, D. (2009). Org. Lett. 11, 4466-4469.]). For related phenyl acrylate compounds, see: Wang et al. (2006[Wang, X.-B. & Kong, L.-Y. (2006). Acta Cryst. E62, o4558-o4559.]); Jones & Jäger (2003[Jones, P. G. & Jäger, S. (2003). Acta Cryst. E59, o369-o371.]). For their biological properties, see: Kim et al. (2004[Kim, J. H., Campbell, B. C., Mahomey, N. E., Chan, K. L. & Molyneux, R. J. (2004). J. Agric. Food Chem. 52, 7814-7821.]); Zhu et al. (2000[Zhu, J., Zhu, H., Kobamoto, N., Yasuda, M. & Tawata, S. (2000). J. Pestic. Sci. 25, 263-266.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18O5

  • Mr = 326.33

  • Triclinic, [P \overline 1]

  • a = 8.4696 (5) Å

  • b = 12.1662 (7) Å

  • c = 16.9860 (9) Å

  • [alpha] = 94.423 (3)°

  • [beta] = 100.038 (3)°

  • [gamma] = 103.475 (3)°

  • V = 1663.33 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • 30114 measured reflections

  • 8303 independent reflections

  • 5258 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.137

  • S = 0.93

  • 8303 reflections

  • 433 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 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
C17A-H17A...O2A 0.93 2.48 3.354 (2) 156
C9A-H9A1...O4Bi 0.97 2.55 3.2215 (16) 126
C19B-H19D...O5Aii 0.96 2.43 3.275 (3) 147
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2375 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics University of Madras, India, for the data collection.

References

Bakthadoss, M., Sivakumar, G. & Kannan, D. (2009). Org. Lett. 11, 4466-4469.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Jones, P. G. & Jäger, S. (2003). Acta Cryst. E59, o369-o371.  [CrossRef] [details]
Kim, J. H., Campbell, B. C., Mahomey, N. E., Chan, K. L. & Molyneux, R. J. (2004). J. Agric. Food Chem. 52, 7814-7821.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, X.-B. & Kong, L.-Y. (2006). Acta Cryst. E62, o4558-o4559.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhu, J., Zhu, H., Kobamoto, N., Yasuda, M. & Tawata, S. (2000). J. Pestic. Sci. 25, 263-266.  [ChemPort]


Acta Cryst (2012). E68, o229  [ doi:10.1107/S1600536811054365 ]

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