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Volume 68 
Part 12 
Page o3403  
December 2012  

Received 5 November 2012
Accepted 13 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.102
Data-to-parameter ratio = 15.2
Details
Open access

(E)-3-(3,5-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one

aJeonju Center, Korea Basic Science Center (KBSI), Jeonju 561-765, Republic of Korea,bDivision of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 143-701, Republic of Korea, and cDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
Correspondence e-mail: dskoh@dongduk.ac.kr

In the title molecule, C21H18O4, the C=C bond of the central enone group adopts a trans conformation. The dihedral angle formed by the naphthalene ring system and the benzene ring is 2.97 (11)°. The hydroxy group 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 [001].

Related literature

For the synthesis and biological properties of chalcone derivatives, see: 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.]); Singh et al. (2012[Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M. S., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594-600.]); Bandgar et al. (2010[Bandgar, B. P., Gawande, S. S., Bodade, R. G., Totre, J. V. & Khobragade, C. N. (2010). Bioorg. Med. Chem. 18, 1364-1370.]); 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.]); Hwang et al. (2011[Hwang, D., Hyun, J., Jo, G., Koh, D. & Lim, Y. (2011). Magn. Reson. Chem. 49, 41-45.]). For related structures, see: 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.]); Jasinski et al. (2011[Jasinski, J. P., Butcher, R. J., Musthafa Khaleel, V., Sarojini, B. K. & Yathirajan, H. S. (2011). Acta Cryst. E67, o845.]). 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
  • C21H18O4

  • Mr = 334.35

  • Orthorhombic, P n a 21

  • a = 30.179 (3) Å

  • b = 3.9127 (3) Å

  • c = 13.7363 (12) Å

  • V = 1622.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 200 K

  • 0.24 × 0.22 × 0.17 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 11095 measured reflections

  • 3479 independent reflections

  • 1828 reflections with I > 2[sigma](I)

  • Rint = 0.064

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

  • wR(F2) = 0.102

  • S = 0.94

  • 3479 reflections

  • 229 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O1 0.84 1.75 2.503 (3) 147
C7-H7C...O1i 0.98 2.59 3.157 (4) 117
C10-H10B...O2i 0.98 2.54 3.344 (4) 139
Symmetry code: (i) [-x+1, -y+3, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. 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: LH5555 ).


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.
Bandgar, B. P., Gawande, S. S., Bodade, R. G., Totre, J. V. & Khobragade, C. N. (2010). Bioorg. Med. Chem. 18, 1364-1370.  [CrossRef] [ChemPort] [PubMed]
Bruker (2000). SMART and SAINT. 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]
Hwang, D., Hyun, J., Jo, G., Koh, D. & Lim, Y. (2011). Magn. Reson. Chem. 49, 41-45.  [ISI] [CrossRef] [ChemPort] [PubMed]
Jasinski, J. P., Butcher, R. J., Musthafa Khaleel, V., Sarojini, B. K. & Yathirajan, H. S. (2011). Acta Cryst. E67, o845.  [CSD] [CrossRef] [details]
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]
Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M. S., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594-600.  [ISI] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3403  [ doi:10.1107/S1600536812046715 ]

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