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Volume 69 
Part 4 
Page o542  
April 2013  

Received 9 February 2013
Accepted 12 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.187
Data-to-parameter ratio = 17.8
Details
Open access

(E)-1-(1-Hydroxynaphthalen-2-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
Correspondence e-mail: dskoh@dongduk.ac.kr

In the title molecule, C22H20O5, the C=C bond of the central enone group adopts an E conformation. The dihedral angle formed by the benzene ring and the naphthalene ring system is 12.6 (4)°. The hydroxy group attached to the naphthalene ring is involved in an intramolecular O-H...O hydrogen bond. In the crystal, weak C-H...O hydrogen bonds link the molecules into chains along [010]. In addition, [pi]-[pi] stacking interactions are present, with centroid-centroid distances of 3.6648 (15) and 3.8661 (15) Å between the benzene and two naphthalene rings.

Related literature

For the synthesis and biological properties of chalcone derivatives, see: Shenvi et al. (2013[Shenvi, S., Kumar, K., Hatti, K. S., Rijesh, K., Diwakar, L. & Reddy, G. C. (2013). Eur. J. Med. Chem. 62, 435-442.]); Hsieh et al. (2012[Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen, C.-T., Wu, S.-F., Wu, Y.-C. & Chang, F.-R. (2012). Bioorg. Med. Chem. Lett. 22, 3912-3915.]); Sharma et al. (2012[Sharma, V., Singh, G., Kaur, H., Saxena, A. K. & Ishar, M. P. S. (2012). Bioorg. Med. Chem. Lett. 22, 6343-6346.]); Sashidhara et al. (2011[Sashidhara, K. V., Kumar, M., Modukuri, R. M., Sonkar, R., Bhatia, G., Khanna, A. K., Rai, S. V. & Shukla, R. (2011). Bioorg. Med. Chem. Lett. 21, 4480-4484.]); Aponte et al. (2010[Aponte, J. C., Castillo, D., Estevez, Y., Gonzalez, G., Arevalo, J., Hammonda, G. B. & Sauvain, M. (2010). Bioorg. Med. Chem. Lett. 20, 100-103.]); Hans et al. (2010[Hans, R. H., Guantai, E. M., Lategan, C., Smith, P. J., Wanc, B., Franzblau, S. G., Gut, J., Rosenthal, P. J. & Chibale, K. (2010). Bioorg. Med. Chem. Lett. 20, 942-944.]) Jo et al. (2012[Jo, G., Sung, S. H., Lee, Y., Kim, B.-G., Yoon, J. W., Lee, H. K., Ji, S. Y., Koh, D., Ahn, J. H. & Lim, Y. (2012). Bull. Korean Chem. Soc. 33, 3841-3844.]). For related structures, see: Park et al. (2013[Park, D. H., Ramkumar, V. & Parthiban, P. (2013). Acta Cryst. E69, o177.]); Fadzillah et al. (2012[Fadzillah, S. M. H., Ngaini, Z., Hussain, H., Razak, I. A. & Asik, S. I. J. (2012). Acta Cryst. E68, o2911-o2912.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C22H20O5

  • Mr = 364.38

  • Monoclinic, P 21 /n

  • a = 9.7919 (12) Å

  • b = 13.7559 (18) Å

  • c = 13.2761 (17) Å

  • [beta] = 96.165 (3)°

  • V = 1777.9 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 200 K

  • 0.36 × 0.26 × 0.22 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.979

  • 12937 measured reflections

  • 4420 independent reflections

  • 2550 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.187

  • S = 1.10

  • 4420 reflections

  • 248 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O5-H5...O1 0.84 1.74 2.490 (2) 147
C21-H21...O3i 0.95 2.43 3.362 (3) 166
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2085 ).


Acknowledgements

The author acknowledges financial support from Dongduk Women's University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Aponte, J. C., Castillo, D., Estevez, Y., Gonzalez, G., Arevalo, J., Hammonda, G. B. & Sauvain, M. (2010). Bioorg. Med. Chem. Lett. 20, 100-103.  [CrossRef] [PubMed] [ChemPort]
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fadzillah, S. M. H., Ngaini, Z., Hussain, H., Razak, I. A. & Asik, S. I. J. (2012). Acta Cryst. E68, o2911-o2912.  [CSD] [CrossRef] [details]
Hans, R. H., Guantai, E. M., Lategan, C., Smith, P. J., Wanc, B., Franzblau, S. G., Gut, J., Rosenthal, P. J. & Chibale, K. (2010). Bioorg. Med. Chem. Lett. 20, 942-944.  [CrossRef] [ChemPort] [PubMed]
Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen, C.-T., Wu, S.-F., Wu, Y.-C. & Chang, F.-R. (2012). Bioorg. Med. Chem. Lett. 22, 3912-3915.  [CrossRef] [ChemPort] [PubMed]
Jo, G., Sung, S. H., Lee, Y., Kim, B.-G., Yoon, J. W., Lee, H. K., Ji, S. Y., Koh, D., Ahn, J. H. & Lim, Y. (2012). Bull. Korean Chem. Soc. 33, 3841-3844.  [ChemPort]
Park, D. H., Ramkumar, V. & Parthiban, P. (2013). Acta Cryst. E69, o177.  [CSD] [CrossRef] [details]
Sashidhara, K. V., Kumar, M., Modukuri, R. M., Sonkar, R., Bhatia, G., Khanna, A. K., Rai, S. V. & Shukla, R. (2011). Bioorg. Med. Chem. Lett. 21, 4480-4484.  [CrossRef] [ChemPort] [PubMed]
Sharma, V., Singh, G., Kaur, H., Saxena, A. K. & Ishar, M. P. S. (2012). Bioorg. Med. Chem. Lett. 22, 6343-6346.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shenvi, S., Kumar, K., Hatti, K. S., Rijesh, K., Diwakar, L. & Reddy, G. C. (2013). Eur. J. Med. Chem. 62, 435-442.  [CrossRef]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o542  [ doi:10.1107/S1600536813006843 ]

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