(Z)-3-Hy­droxy-4-(4-meth­oxy­phen­yl)but-3-en-2-one

Fang, W.; Hu, J.-P.; Wang, M.; Chen, M.-Z.

doi:10.1107/S1600536813002262

Volume 69
Part 3
Page o359
March 2013

Received 3 January 2013
Accepted 23 January 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.113
Data-to-parameter ratio = 14.1
Details

(Z)-3-Hydroxy-4-(4-methoxyphenyl)but-3-en-2-one

Wei Fang,^a Jun-Ping Hu,^b Mei Wang ^a and Mu-Zi Chen ^a ^*

^aAnalysis and Testing Center, Dushu Lake Campus, Suzhou University, Suzhou 215123, People's Republic of China, and ^bDepartment of Chemistry, Handan College, Hebei Handan 056002, People's Republic of China
Correspondence e-mail: chenmuzi@suda.edu.cn

The title compound, C₁₁H₁₂O₃, is potentially a butane-2,3-dione derivative but exists in the enol form in the solid state. In the molecule, the 3-hydroxybut-3-en-2-one, benzene and methoxyl fragments are almost co-planar. The 3-hydroxybut-3-en-2-one fragment is almost planar with an r.m.s. deviation of 0.040 Å. The dihedral angle between this plane and that of the benzene ring is 5.88 (4)°. The 4-methoxy group also lies close to the benzene ring plane, with deviations of 0.0206 (11) Å for the O and 0.087 (2) Å for methyl C atoms. Hence, the whole molecule is almost planar with an r.m.s. deviation of 0.0617 Å from a plane through all 14 non-H atoms. In the crystal, the molecules are linked by O-HO hydrogen bonds, generating [010] chains.

Related literature

The synthesis of the compound is described by Wang & Huang (2010). For applications of aromatic ketones as fragrances, see: Tong et al. (2009). For the relationship between structure and fragrance, see: Griesbeck et al. (2012). For related structures and details of their synthesis, see: Yamane et al. (2005); Si et al. (1990); Salimbeni et al. (1987); Mosrin et al. (2009). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₂O₃
M_r = 192.21
Monoclinic, P 2₁ /c
a = 18.8076 (13) Å
b = 5.3007 (4) Å
c = 10.1439 (8) Å
= 103.425 (7)°
V = 983.65 (13) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 223 K
0.50 × 0.40 × 0.35 mm

Data collection

Agilent Xcalibur (Atlas CCD, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.915, T_max = 1.000
6213 measured reflections
1829 independent reflections
1505 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.113
S = 1.01
1829 reflections
130 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	0.82	2.27	3.0315 (17)	154
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5292 ).

Acknowledgements

This work was supported by the Natural Science Foundation of China (NSFC) (grant 21203130).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
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.
Brandenburg, K. (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Griesbeck, A. G., Hinze, O., Görner, H., Huchel, U., Kropf, C., Sundermeier, U. & Gerke, T. (2012). Photochem. Photobiol. Sci. 11, 587-592.
Mosrin, M., Bresser, T. & Knochel, P. (2009). Org. Lett. 11, 3406-3409.
Salimbeni, A., Manghisi, E., Fregnan, G. B. & Prada, M. (1987). J. Med. Chem. 30, 773-780.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Si, Z. X., Jiao, X. Y. & Hu, B. F. (1990). Synthesis, 6, 509-510.
Tong, X. L., Xu, J., Miao, H., Gao, J., Sun, Z. Q. & Zhang, W. (2009). J. Chem. Technol. Biotechnol. 84, 1762-1766.
Wang, S. P. & Huang, Z.-Q. (2010). Chinese Patent 200910111432, Bestally Biotechnology Co. Ltd.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Yamane, M., Uera, K. & Narasaka, K. (2005). Bull. Chem. Soc. Jpn, 78, 477-486.

organic compounds