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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 [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.113
Data-to-parameter ratio = 14.1
Details
Open access

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

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-H...O hydrogen bonds, generating [010] chains.

Related literature

The synthesis of the compound is described by Wang & Huang (2010[Wang, S. P. & Huang, Z.-Q. (2010). Chinese Patent 200910111432, Bestally Biotechnology Co. Ltd.]). For applications of aromatic ketones as fragrances, see: Tong et al. (2009[Tong, X. L., Xu, J., Miao, H., Gao, J., Sun, Z. Q. & Zhang, W. (2009). J. Chem. Technol. Biotechnol. 84, 1762-1766.]). For the relationship between structure and fragrance, see: Griesbeck et al. (2012[Griesbeck, A. G., Hinze, O., Görner, H., Huchel, U., Kropf, C., Sundermeier, U. & Gerke, T. (2012). Photochem. Photobiol. Sci. 11, 587-592.]). For related structures and details of their synthesis, see: Yamane et al. (2005[Yamane, M., Uera, K. & Narasaka, K. (2005). Bull. Chem. Soc. Jpn, 78, 477-486.]); Si et al. (1990[Si, Z. X., Jiao, X. Y. & Hu, B. F. (1990). Synthesis, 6, 509-510.]); Salimbeni et al. (1987[Salimbeni, A., Manghisi, E., Fregnan, G. B. & Prada, M. (1987). J. Med. Chem. 30, 773-780.]); Mosrin et al. (2009[Mosrin, M., Bresser, T. & Knochel, P. (2009). Org. Lett. 11, 3406-3409.]). 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
  • C11H12O3

  • Mr = 192.21

  • Monoclinic, P 21 /c

  • a = 18.8076 (13) Å

  • b = 5.3007 (4) Å

  • c = 10.1439 (8) Å

  • [beta] = 103.425 (7)°

  • V = 983.65 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.915, Tmax = 1.000

  • 6213 measured reflections

  • 1829 independent reflections

  • 1505 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.113

  • S = 1.01

  • 1829 reflections

  • 130 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 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[Agilent (2012). 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: DIAMOND (Brandenburg, 2004[Brandenburg, K. (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort] [PubMed]
Mosrin, M., Bresser, T. & Knochel, P. (2009). Org. Lett. 11, 3406-3409.  [ISI] [CrossRef] [PubMed] [ChemPort]
Salimbeni, A., Manghisi, E., Fregnan, G. B. & Prada, M. (1987). J. Med. Chem. 30, 773-780.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Si, Z. X., Jiao, X. Y. & Hu, B. F. (1990). Synthesis, 6, 509-510.  [CrossRef]
Tong, X. L., Xu, J., Miao, H., Gao, J., Sun, Z. Q. & Zhang, W. (2009). J. Chem. Technol. Biotechnol. 84, 1762-1766.  [CrossRef] [ChemPort]
Wang, S. P. & Huang, Z.-Q. (2010). Chinese Patent 200910111432, Bestally Biotechnology Co. Ltd.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yamane, M., Uera, K. & Narasaka, K. (2005). Bull. Chem. Soc. Jpn, 78, 477-486.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o359  [ doi:10.1107/S1600536813002262 ]

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