[Journal logo]

Volume 64 
Part 9 
Page o1834  
September 2008  

Received 12 August 2008
Accepted 20 August 2008
Online 30 August 2008

[bx2172sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.064
wR = 0.139
Data-to-parameter ratio = 12.8
Details
Open access

(E)-3-(2,3-Dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one

Carlos A. Escobar,a* Andrés Vega,a Dieter Sickerb and Andrés Ibañezc

aUniversidad Andres Bello, Departamento de Ciencias Químicas, Santiago, Chile,bInstitut für Organische Chemie, Universität Leipzig, D-04103 Leipzig, Germany, and cLaboratorio de Cristalografía, Departamento de Física, Facultad de Ciencias Físicas y Matemáticas, Universidad de Chile
Correspondence e-mail: cescobar@unab.cl

The molecular conformation of the title compound, C18H18O5, is stabilized by a strong intramolecular hydrogen bond between the hydroxyl and carbonyl groups. The C=C double bond displays an E configuration while the carbonyl group shows an S-cis configuration relative to the double bond. The dihedral angle between the two rings is 15.0 (1)°.

Related literature

For related literature, see: Chu et al. (2004[Chu, H.-W., Wu, H.-T. & Lee, Y.-J. (2004). Tetrahedron, 60, 2647-2655.]); Desiraju (2002[Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.]); Fronczek et al. (1987[Fronczek, F. R., Tanrisever, N. & Fischer, N. H. (1987). Acta Cryst. C43, 158-160.]); Radha Krishna et al. (2005[Radha Krishna, J., Jagadeesh Kumar, N., Krishnaiah, M., Venkata Rao, C., Koteswara Rao, Y. & Puranik, V. G. (2005). Acta Cryst. E61, o1323-o1325.]); Rao et al. (2004[Rao, Y. K., Fang, S.-H. & Tzeng, Y.-M. (2004). Bioorg. Med. Chem. 12, 2679-2686.]); Shoja (1999[Shoja, M. (1999). Z. Kristallogr. 214, 235-240.]); Subbiah Pandi et al. (2003[Subbiah Pandi, A., Velmurugan, D., Shanmuga Sundara Raj, S., Fun, H.-K. & Bansal, M. C. (2003). Acta Cryst. C59, o302-o304.]); Usman et al. (2006[Usman, H., Jalaluddin, M. N., Hakim, E. H., Syah, Y. M. & Yamin, B. M. (2006). Acta Cryst. E62, o209-o211.]); Wafo et al. (2005[Wafo, P., Hussain, H., Kouam, S. F., Ngadjui, B. T., Flörke, U. & Krohn, K. (2005). Acta Cryst. E61, o3017-o3019.]); Wallet et al. (1995[Wallet, J.-C., Molins, E. & Miravitlles, C. (1995). Acta Cryst. C51, 123-125.]); Wu et al. (2005[Wu, H., Xu, Z. & Liang, Y.-M. (2005). Acta Cryst. E61, o1434-o1435.]).

[Scheme 1]

Experimental

Crystal data

  • C18H18O5

  • Mr = 314.32

  • Monoclinic, P 21 /c

  • a = 4.8793 (5) Å

  • b = 24.283 (3) Å

  • c = 13.0770 (14) Å

  • [beta] = 97.044 (2)°

  • V = 1537.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 150 (2) K

  • 0.25 × 0.10 × 0.07 mm
Data collection

  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SAINT-NT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.993

  • 9482 measured reflections

  • 2717 independent reflections

  • 1522 reflections with I > 2[sigma](I)

  • Rint = 0.080
Refinement

  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.139

  • S = 1.03

  • 2717 reflections

  • 212 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O20-H20...O1 0.84 1.77 2.515 (3) 147

Data collection: SMART-NT (Bruker, 2001[Bruker (2001). SMART-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 1999[Bruker (1999). SAINT-NT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2172 ).

Acknowledgements

The authors gratefully acknowledge generous financial support from FONDECYT (grant No. 1080147) and Universidad Andres Bello (grant No. DI-UNAB-20-06/R).

References

Bruker (1999). SAINT-NT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SMART-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chu, H.-W., Wu, H.-T. & Lee, Y.-J. (2004). Tetrahedron, 60, 2647-2655.  [ISI] [CSD] [CrossRef] [ChemPort]
Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.  [ISI] [CrossRef] [PubMed] [ChemPort]
Fronczek, F. R., Tanrisever, N. & Fischer, N. H. (1987). Acta Cryst. C43, 158-160.  [CrossRef] [details]
Radha Krishna, J., Jagadeesh Kumar, N., Krishnaiah, M., Venkata Rao, C., Koteswara Rao, Y. & Puranik, V. G. (2005). Acta Cryst. E61, o1323-o1325.  [CSD] [CrossRef] [details]
Rao, Y. K., Fang, S.-H. & Tzeng, Y.-M. (2004). Bioorg. Med. Chem. 12, 2679-2686.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shoja, M. (1999). Z. Kristallogr. 214, 235-240.  [ChemPort]
Subbiah Pandi, A., Velmurugan, D., Shanmuga Sundara Raj, S., Fun, H.-K. & Bansal, M. C. (2003). Acta Cryst. C59, o302-o304.  [CSD] [CrossRef] [ChemPort] [details]
Usman, H., Jalaluddin, M. N., Hakim, E. H., Syah, Y. M. & Yamin, B. M. (2006). Acta Cryst. E62, o209-o211.  [CrossRef] [details]
Wafo, P., Hussain, H., Kouam, S. F., Ngadjui, B. T., Flörke, U. & Krohn, K. (2005). Acta Cryst. E61, o3017-o3019.  [CrossRef] [details]
Wallet, J.-C., Molins, E. & Miravitlles, C. (1995). Acta Cryst. C51, 123-125.  [CrossRef] [details]
Wu, H., Xu, Z. & Liang, Y.-M. (2005). Acta Cryst. E61, o1434-o1435.  [CSD] [CrossRef] [details]

Acta Cryst (2008). E64, o1834  [ doi:10.1107/S1600536808026949 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.