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

Anuradha, T.; Sivakumar, G.; Seshadri, P.R.; Bakthadoss, M.

doi:10.1107/S1600536811054365

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 (C-C) = 0.002 Å
R = 0.044
wR = 0.137
Data-to-parameter ratio = 19.2
Details

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

T. Anuradha,^a G. Sivakumar,^b P. R. Seshadri ^a ^* and M. Bakthadoss ^b

^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-HO hydrogen-bond occurs in molecule A. The crystal packing features intermolecular C-HO interactions.

Related literature

For background to the synthesis, see: Bakthadoss et al. (2009). For related phenyl acrylate compounds, see: Wang et al. (2006); Jones & Jäger (2003). For their biological properties, see: Kim et al. (2004); Zhu et al. (2000).

Experimental

Crystal data

C₁₉H₁₈O₅
M_r = 326.33
Triclinic, $[P \overline 1]$
a = 8.4696 (5) Å
b = 12.1662 (7) Å
c = 16.9860 (9) Å
= 94.423 (3)°
= 100.038 (3)°
= 103.475 (3)°
V = 1663.33 (16) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.137
S = 0.93
8303 reflections
433 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C17A-H17AO2A	0.93	2.48	3.354 (2)	156
C9A-H9A1O4Bⁱ	0.97	2.55	3.2215 (16)	126
C19B-H19DO5Aⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); 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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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

organic compounds