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

Lee, H.-J.; Lim, Y.; Koh, D.

doi:10.1107/S1600536812046715

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 (C-C) = 0.004 Å
R = 0.044
wR = 0.102
Data-to-parameter ratio = 15.2
Details

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

Ha-Jin Lee,^a Yoongho Lim ^b and Dongsoo Koh ^c ^*

^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-HO hydrogen bond. In the crystal, weak C-HO 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); Singh et al. (2012); Bandgar et al. (2010); Hans et al. (2010); Hwang et al. (2011). For related structures, see: Fadzillah et al. (2012); Jasinski et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₂₁H₁₈O₄
M_r = 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 radiation
= 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(I)
R_int = 0.064

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.102
S = 0.94
3479 reflections
229 parameters
1 restraint
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4O1	0.84	1.75	2.503 (3)	147
C7-H7CO1ⁱ	0.98	2.59	3.157 (4)	117
C10-H10BO2ⁱ	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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
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.
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, D., Hyun, J., Jo, G., Koh, D. & Lim, Y. (2011). Magn. Reson. Chem. 49, 41-45.
Jasinski, J. P., Butcher, R. J., Musthafa Khaleel, V., Sarojini, B. K. & Yathirajan, H. S. (2011). Acta Cryst. E67, o845.
Sharma, V., Singh, G., Kaur, H., Saxena, A. K. & Ishar, M. P. S. (2012). Bioorg. Med. Chem. Lett. 22, 6343-6346.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds