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Volume 68 
Part 11 
Page o3126  
November 2012  

Received 1 October 2012
Accepted 8 October 2012
Online 13 October 2012

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.043
wR = 0.127
Data-to-parameter ratio = 26.5
Details
Open access

1-(2-Hydroxy-5-methoxyphenyl)-3-methylbut-2-en-1-one1

Catherine Thomas Alexander,a David Vargas,a Frank R. Fronczeka* and Steven F. Watkinsa

aDepartment of Chemistry, Louisiana State University, Baton Rouge LA 70803-1804 USA
Correspondence e-mail: ffroncz@lsu.edu

The title compound, C12H14O3, is a natural product derived from the medium-sized hawthorn Crataegus persimilis ('prunifolia'). The mean plane of the butene moiety is twisted by 13.27 (7)° with respect to the that of the dioxobenzaldehyde moiety. There is an intramolecular hydrogen bond between the hydroxyl group and the carbonyl O atom.

Related literature

For isolation from plant material, see: Castro et al. (1989[Castro, V., Tamayo-Castillo, G. & Jakupovic, J. (1989). Phytochemistry, 28, 2415-2418.]). For the synthesis, see: Camps et al. (1985[Camps, F., Coll, J., Colomina, O. & Messeguer, A. (1985). J. Heterocycl. Chem. 22, 363-368.]). For photolysis to form 4-chromanones, see: Primo et al. (1982[Primo, J., Tormo, R. & Miranda, M. A. (1982). Heterocycles, 19, 1819-1822.]). For a related structure, see: Zeller et al. (2010[Zeller, M., Sridharan, M., Rajendra Prasad, K. J. & Ngendahimana, A. (2010). Acta Cryst. E66, o297-o298.]).

[Scheme 1]

Experimental

Crystal data

  • C12H14O3

  • Mr = 206.23

  • Monoclinic, P 21 /c

  • a = 14.027 (3) Å

  • b = 5.816 (1) Å

  • c = 12.829 (3) Å

  • [beta] = 91.409 (8)°

  • V = 1046.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.45 × 0.37 × 0.23 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.959, Tmax = 0.979

  • 6425 measured reflections

  • 3784 independent reflections

  • 3179 reflections with I > 2[sigma](I)

  • Rint = 0.018
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.127

  • S = 1.04

  • 3784 reflections

  • 143 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O3 0.87 (2) 1.74 (2) 2.523 (1) 149 (2)

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2405 ).

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF (1999-2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Camps, F., Coll, J., Colomina, O. & Messeguer, A. (1985). J. Heterocycl. Chem. 22, 363-368.  [CrossRef] [ChemPort]
Castro, V., Tamayo-Castillo, G. & Jakupovic, J. (1989). Phytochemistry, 28, 2415-2418.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Primo, J., Tormo, R. & Miranda, M. A. (1982). Heterocycles, 19, 1819-1822.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zeller, M., Sridharan, M., Rajendra Prasad, K. J. & Ngendahimana, A. (2010). Acta Cryst. E66, o297-o298.  [CSD] [CrossRef] [details]

Acta Cryst (2012). E68, o3126  [ doi:10.1107/S1600536812042158 ]

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