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Volume 69 
Part 5 
Page o715  
May 2013  

Received 5 March 2013
Accepted 7 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 290 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.055
wR = 0.161
Data-to-parameter ratio = 12.6
Details
Open access

(E)-1-[2-Hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-phenylprop-2-en-1-one

aKey Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, University of Chinese Academy of Sciences, People's Republic of China, and bState Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, People's Republic of China
Correspondence e-mail: haji@ms.xjb.ac.cn

The title compound, C19H20O6, consists of a tetrasubstituted benzene ring with one substituent being an [alpha],[beta]-unsaturated cinnamoyl group, which forms an extended conjugated system in the molecule. In addition, two methoxymethoxy and one hydroxy group are bonded to the central benzene ring. The dihedral angle between eh rings is 10.22 (10)°. An intramolecular hydrogen bond is observed between the hydroxy group and the carbonyl O atom. One of the methoxymethoxy substituents is conformationally disordered over two sets of sites with site-occupation factors of 0.831 (3) and 0.169 (3).

Related literature

For the preparation of the title compound, see: Sui et al. (2012[Sui, X., Quan, Y. C., Chang, Y., Zhang, R. P., Xu, Y. F. & Guan, L. P. (2012). Med. Chem. Res. 21, 1290-1296.]). For general background to the biological activity of chalcones which posess more than one hydroxy substituent, see: Jun et al. (2007[Jun, N., Hong, G. & Jun, K. (2007). Bioorg. Med. Chem. 15, 2396-2402.]); Jin et al. (2007[Jin, F., Jin, X. Y., Jin, Y. L., Sohn, D. W., Kim, S. A., Sohn, D. H., Kim, Y. C. & Kim, H. S. (2007). Arch. Pharm. Res. 30, 1359-1367.]); Urgaonkar et al. (2005[Urgaonkar, S., La Pierre, H. S., Meir, I., Lund, H., RayChaudhuri, D. & Shaw, J. T. (2005). Org. Lett. 7, 5609-5612.]); Nerya et al. (2004[Nerya, O., Musa, R., Khatib, S., Tamir, S. & Vaya, J. (2004). Phytochemistry, 65, 1389-1395.], 2003[Nerya, O., Vaya, J., Musa, R., Izrael, S., Ben-Arie, R. & Tamir, S. (2003). J. Agric. Food. Chem. 51, 1201-1207.]); Khatib et al. (2005[Khatib, S., Nerya, O., Musa, R., Shmuel, M., Tamir, S. & Vaya, J. (2005). Bioorg. Med. Chem. 13, 433-441.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20O6

  • Mr = 344.35

  • Monoclinic, P 21 /n

  • a = 8.7791 (2) Å

  • b = 9.7807 (2) Å

  • c = 20.2209 (4) Å

  • [beta] = 96.792 (2)°

  • V = 1724.10 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.82 mm-1

  • T = 290 K

  • 0.45 × 0.40 × 0.32 mm

Data collection
  • Agilent Gemini S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.] Tmin = 0.709, Tmax = 0.779

  • 5842 measured reflections

  • 2964 independent reflections

  • 2492 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.161

  • S = 1.02

  • 2964 reflections

  • 235 parameters

  • 37 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 0.82 1.73 2.466 (2) 148

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2424 ).


Acknowledgements

This work was supported by a grant from the Xinjiang Natural Science Foundation (No. 2009211B34), the China National Science Fund for Distinguished Young Scholars (No. 30925045), the National Basic Research Program of China (No. 2011CB512013) and the CAS/SAFEA International Partnership Program for Creative Research Teams (2008-18).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jin, F., Jin, X. Y., Jin, Y. L., Sohn, D. W., Kim, S. A., Sohn, D. H., Kim, Y. C. & Kim, H. S. (2007). Arch. Pharm. Res. 30, 1359-1367.  [CrossRef] [PubMed] [ChemPort]
Jun, N., Hong, G. & Jun, K. (2007). Bioorg. Med. Chem. 15, 2396-2402.  [CrossRef] [PubMed] [ChemPort]
Khatib, S., Nerya, O., Musa, R., Shmuel, M., Tamir, S. & Vaya, J. (2005). Bioorg. Med. Chem. 13, 433-441.  [CrossRef] [PubMed] [ChemPort]
Nerya, O., Musa, R., Khatib, S., Tamir, S. & Vaya, J. (2004). Phytochemistry, 65, 1389-1395.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nerya, O., Vaya, J., Musa, R., Izrael, S., Ben-Arie, R. & Tamir, S. (2003). J. Agric. Food. Chem. 51, 1201-1207.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sui, X., Quan, Y. C., Chang, Y., Zhang, R. P., Xu, Y. F. & Guan, L. P. (2012). Med. Chem. Res. 21, 1290-1296.  [ISI] [CrossRef] [ChemPort]
Urgaonkar, S., La Pierre, H. S., Meir, I., Lund, H., RayChaudhuri, D. & Shaw, J. T. (2005). Org. Lett. 7, 5609-5612.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o715  [ doi:10.1107/S1600536813009380 ]

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