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Volume 69 
Part 11 
Pages o1657-o1658  
November 2013  

Received 11 September 2013
Accepted 1 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.052
wR = 0.121
Data-to-parameter ratio = 8.6
Details
Open access

(6S*)-6-[(1S*,2R*)-1,2-Di­hydroxy­pent­yl]-4-meth­oxy-5,6-di­hydro-2H-pyran-2-one

aDepartment of Chemistry, University of Central Florida, 4104 Libra Drive, Orlando, FL 32816, USA,bUniversity of Utah, Department of Chemistry, 315 S. 1400 E. Rm. 2020, Salt Lake City, UT 84112, USA, and cDepartment of Plant Sciences and Plant Pathology, Montana State University, 206 Plant Bioscience Building, Bozeman, MT 59717, USA
Correspondence e-mail: James.Harper@ucf.edu

The title compound, C11H18O5, was isolated from a liquid culture of Pestalotiopsis sp. In the mol­ecule, the pyran-2-one ring assumes a half-chair conformation. The two terminal C atoms of the pentyl group were refined as disordered over two sets of sites, with refined occupancies of 0.881 (10) and 0.119 (10). In the crystal, mol­ecules are linked via O-H...O hydrogen bonds forming a three-dimensional network.

Related literature

For the first isolation of the title compound, see: McGahren et al. (1973[McGahren, W. J., Ellestad, G. A., Morton, G. O., Kunstmann, M. P. & Mullen, P. (1973). J. Org. Chem. 38, 3542-3544.]). For the natural and unnatural stereospecific synthesis, see: Kirihata et al. (1990[Kirihata, M., Ohta, K., Ichimoto, I. & Ueda, H. (1990). Agric. Biol. Chem. 54, 2401-2405.], 1992a[Kirihata, M., Kamihisa, Y., Ichimoto, I. & Ueda, H. (1992a). Chem. Express, 7, 837-840.],b[Kirihata, M., Ohe, M., Ichimoto, I. & Ueda, H. (1992b). Biosci. Biotechnol. Biochem. 56, 1825-1828.]); Masaki et al. (1994[Masaki, Y., Imaeda, T. & Kawai, M. (1994). Chem. Pharm. Bull. 42, 179-181.]). For closely related products from other fungi, see: Kimura et al. (1986[Kimura, Y., Hamasaki, T. & Nakajima, H. (1986). Agric. Biol. Chem. 50, 1649-1650.]); Kirihata et al. (1996[Kirihata, M., Ohe, M., Ichimoto, I. & Kinura, Y. (1996). Biosci. Biotechnol. Biochem. 60, 677-679.]); Lee et al. (1995[Lee, J. C., Yang, X., Schwartz, M., Strobel, G. & Clardy, J. (1995). Chem. Biol. 2, 721-727.]); Davies-Coleman & Rivett (1989[Davies-Coleman, M. T. & Rivett, D. E. A. (1989). Progress in the Chemistry of Organic Natural Products, Vol. 55, edited by W. Herz, H. Grise, G. W. Kirby & Ch. Tamm, pp. 1-35. Berlin: Springer-Verlag.]). For biological activity, see: Venkatasubbaiah & Van Dyke (1991[Venkatasubbaiah, P. & Van Dyke, C. G. (1991). Phytochemistry, 30, 1471-1474.]). For crystal structures of related compounds, see: Yoshino & Nowacki (1972[Yoshino, A. & Nowacki, W. (1972). Z. Kristallogr. 136, 66-80.]); Engel & Nowacki (1972a[Engel, P. & Nowacki, W. (1972a). Z. Kristallogr. 136, 437-452.],b[Engel, P. & Nowacki, W. (1972b). Z. Kristallogr. 136, 453-467.]).

[Scheme 1]

Experimental

Crystal data
  • C11H18O5

  • Mr = 230.25

  • Orthorhombic, P 21 21 21

  • a = 5.0375 (3) Å

  • b = 11.4515 (13) Å

  • c = 20.802 (2) Å

  • V = 1200.02 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 200 K

  • 0.28 × 0.18 × 0.08 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO-SMN; 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 = 0.973, Tmax = 0.992

  • 2711 measured reflections

  • 1616 independent reflections

  • 1153 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.121

  • S = 1.06

  • 1616 reflections

  • 188 parameters

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1'-H1'O...O2i 0.85 (3) 1.93 (3) 2.778 (3) 177 (3)
O2'-H2'O...O2'ii 0.80 (4) 2.05 (4) 2.8178 (18) 163 (4)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (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-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5653 ).


References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Davies-Coleman, M. T. & Rivett, D. E. A. (1989). Progress in the Chemistry of Organic Natural Products, Vol. 55, edited by W. Herz, H. Grise, G. W. Kirby & Ch. Tamm, pp. 1-35. Berlin: Springer-Verlag.
Engel, P. & Nowacki, W. (1972a). Z. Kristallogr. 136, 437-452.  [CrossRef] [ChemPort]
Engel, P. & Nowacki, W. (1972b). Z. Kristallogr. 136, 453-467.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kimura, Y., Hamasaki, T. & Nakajima, H. (1986). Agric. Biol. Chem. 50, 1649-1650.  [CrossRef] [ChemPort]
Kirihata, M., Kamihisa, Y., Ichimoto, I. & Ueda, H. (1992a). Chem. Express, 7, 837-840.  [ChemPort]
Kirihata, M., Ohe, M., Ichimoto, I. & Kinura, Y. (1996). Biosci. Biotechnol. Biochem. 60, 677-679.  [CrossRef] [ChemPort]
Kirihata, M., Ohe, M., Ichimoto, I. & Ueda, H. (1992b). Biosci. Biotechnol. Biochem. 56, 1825-1828.  [CrossRef] [ChemPort]
Kirihata, M., Ohta, K., Ichimoto, I. & Ueda, H. (1990). Agric. Biol. Chem. 54, 2401-2405.  [CrossRef] [ChemPort]
Lee, J. C., Yang, X., Schwartz, M., Strobel, G. & Clardy, J. (1995). Chem. Biol. 2, 721-727.  [CrossRef] [ChemPort] [PubMed]
Masaki, Y., Imaeda, T. & Kawai, M. (1994). Chem. Pharm. Bull. 42, 179-181.  [CrossRef] [ChemPort] [PubMed]
McGahren, W. J., Ellestad, G. A., Morton, G. O., Kunstmann, M. P. & Mullen, P. (1973). J. Org. Chem. 38, 3542-3544.  [CrossRef] [ChemPort] [PubMed]
Nonius (1998). 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Venkatasubbaiah, P. & Van Dyke, C. G. (1991). Phytochemistry, 30, 1471-1474.  [CrossRef] [ChemPort] [Web of Science]
Yoshino, A. & Nowacki, W. (1972). Z. Kristallogr. 136, 66-80.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1657-o1658   [ doi:10.1107/S1600536813027025 ]

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