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Volume 69 
Part 9 
Page o1406  
September 2013  

Received 19 July 2013
Accepted 29 July 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.114
Data-to-parameter ratio = 13.2
Details
Open access

Levulinic acid

aInstitute of Chemistry, University of Silesia, 14 Bankowa Street, 40-006 Katowice, Poland, and bInstitute of Physics, University of Silesia, 4 Uniwersytecka Street, 40-007 Katowice, Poland
Correspondence e-mail: bhachula@o2.pl

The title compound (systematic name: 4-oxopentanoic acid), C5H8O3, is close to planar (r.m.s. deviation = 0.0762 Å). In the crystal, the molecules interact via O-H...O hydrogen bonds in which the hydroxy O atoms act as donors and the ketone O atoms in adjacent molecules as acceptors, forming C(7) chains along [20-1].

Related literature

For uses of levulinic acid, see: Timokhin et al. (1999[Timokhin, B. V., Baransky, V. A. & Eliseeva, G. D. (1999). Russ. Chem. Rev. 68, 73-84.]). For density functional and Møller-Plesset perturbation theory calculations for levulinic acid, see: Reichert et al. (2010[Reichert, D., Montoya, A., Liang, X., Bockhorn, H. & Haynes, B. S. (2010). J. Phys. Chem. A, 114, 12323-12329.]); Kim et al. (2011[Kim, T., Assary, R. S., Curtiss, L. A., Marshall, C. L. & Stair, P. C. (2011). J. Raman Spectrosc. 42, 2069-2076.]). For typical bond lengths and angles, see: Allen et al. (1987[Allen, F. A., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Borthwick (1980[Borthwick, P. W. (1980). Acta Cryst. B36, 628-632.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]). For background to the study, see: Flakus & Hachula (2008[Flakus, H. & Hachula, B. (2008). Chem. Phys. B345, 49-64.]); Flakus & Stachowska (2006[Flakus, H. & Stachowska, B. (2006). Chem. Phys. B330, 231-244.]).

[Scheme 1]

Experimental

Crystal data
  • C5H8O3

  • Mr = 116.11

  • Monoclinic, P 21 /c

  • a = 4.8761 (2) Å

  • b = 12.1025 (4) Å

  • c = 9.8220 (3) Å

  • [beta] = 99.112 (3)°

  • V = 572.31 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.44 × 0.21 × 0.16 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire3 detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]) Tmin = 0.585, Tmax = 1.000

  • 7178 measured reflections

  • 1013 independent reflections

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

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.114

  • S = 1.06

  • 1013 reflections

  • 77 parameters

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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3i 0.83 (2) 1.87 (2) 2.6977 (13) 176 (2)
Symmetry code: (i) [x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]); data reduction: CrysAlis RED; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); 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: FF2114 ).


References

Allen, F. A., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Borthwick, P. W. (1980). Acta Cryst. B36, 628-632.  [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Flakus, H. & Hachula, B. (2008). Chem. Phys. B345, 49-64.  [ISI] [CrossRef]
Flakus, H. & Stachowska, B. (2006). Chem. Phys. B330, 231-244.  [ISI] [CrossRef]
Kim, T., Assary, R. S., Curtiss, L. A., Marshall, C. L. & Stair, P. C. (2011). J. Raman Spectrosc. 42, 2069-2076.  [ISI] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.
Reichert, D., Montoya, A., Liang, X., Bockhorn, H. & Haynes, B. S. (2010). J. Phys. Chem. A, 114, 12323-12329.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Timokhin, B. V., Baransky, V. A. & Eliseeva, G. D. (1999). Russ. Chem. Rev. 68, 73-84.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1406  [ doi:10.1107/S1600536813021090 ]

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