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Volume 69 
Part 6 
Page o952  
June 2013  

Received 9 May 2013
Accepted 17 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.084
Data-to-parameter ratio = 14.4
Details
Open access

Acetoxy-[gamma]-valerolactone

aCarbohydrate Chemistry Group, Callaghan Innovation Research Limited, PO Box 31-310, Lower Hutt, New Zealand
Correspondence e-mail: graeme.gainsford@callaghaninnovation.govt.nz

Levulinyl cellulose esters have been produced as an effective renewable binder for architectural coatings. The title compound, C7H10O4 (systematic name: 2-methyl-5-oxotetrahydrofuran-2-yl acetate), assigned as the esterifying species, was isolated and crystallized to confirm the structure. In the crystal, the molecules pack in layers parallel to (102) utilizing weak C-H...O interactions.

Related literature

For related structures, see: Cai et al. (2004[Cai, Y., Roberts, B. P., Tocher, D. A. & Barnett, S. A. (2004). Org. Biomol. Chem. 2, 2517-2529.]). For hydrogen-bonding motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For background information, see: Bredt (1886[Bredt, J. (1886). Ann. Chem. 236, 225-232.]); Rasmussen & Brattain (1949[Rasmussen, R. S. & Brattain, R. R. (1949). J. Am. Chem. Soc. 71, 1073-1079.]); Suami & Day (1959[Suami, T. & Day, A. R. (1959). J. Org. Chem. 24, 1340-1343.]); Glenny et al. (2012[Glenny, M., Gooch, C., Hinkley, S., Mason, J., Tristram, C. & Williams, D. (2012). NZ Patent No. PCT/NZ2012/000728.]). For a previous description of the title compound but without supporting crystal structure data, see: Bell & Covington (1975[Bell, R. P. & Covington, A. D. (1975). J. Chem. Soc. Perkin Trans. 2, pp. 1343-1348.]).

[Scheme 1]

Experimental

Crystal data
  • C7H10O4

  • Mr = 158.15

  • Monoclinic, P 21 /c

  • a = 5.86715 (15) Å

  • b = 12.7280 (3) Å

  • c = 10.2756 (3) Å

  • [beta] = 106.020 (3)°

  • V = 737.55 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.00 mm-1

  • T = 120 K

  • 0.19 × 0.12 × 0.07 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: gaussian (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.812, Tmax = 1.000

  • 4959 measured reflections

  • 1469 independent reflections

  • 1350 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.084

  • S = 1.03

  • 1469 reflections

  • 102 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 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
C3-H3B...O2i 0.99 2.68 3.5827 (13) 152
C1-H1B...O3ii 0.98 2.63 3.4617 (14) 142
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Ltd, 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: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP in WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL2012 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5410 ).


Acknowledgements

We thank Dr Matthew Polson of the University of Canterbury, New Zealand, for the data collection.

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Bell, R. P. & Covington, A. D. (1975). J. Chem. Soc. Perkin Trans. 2, pp. 1343-1348.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bredt, J. (1886). Ann. Chem. 236, 225-232.
Cai, Y., Roberts, B. P., Tocher, D. A. & Barnett, S. A. (2004). Org. Biomol. Chem. 2, 2517-2529.  [CSD] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Glenny, M., Gooch, C., Hinkley, S., Mason, J., Tristram, C. & Williams, D. (2012). NZ Patent No. PCT/NZ2012/000728.
Rasmussen, R. S. & Brattain, R. R. (1949). J. Am. Chem. Soc. 71, 1073-1079.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Suami, T. & Day, A. R. (1959). J. Org. Chem. 24, 1340-1343.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o952  [ doi:10.1107/S1600536813013561 ]

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