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Volume 69 
Part 6 
Pages o872-o873  
June 2013  

Received 14 January 2013
Accepted 6 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.093
Data-to-parameter ratio = 10.6
Details
Open access

Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate

aSchool of Biotechnology and Biomolecular Sciences, University of New South Wales, Sydney, NSW 2052, Australia, and bMark Wainwright Analytical Centre, University of New South Wales, Sydney, NSW 2052, Australia
Correspondence e-mail: b.neilan@unsw.edu.au

The title compound (systematic name: 3,7-dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one dimethyl sulfoxide monosolvate), C15H12O5·C2H6OS, was isolated from an unidentified endophytic fungus (belonging to class Ascomycetes) of Taxus sp. In the crystal, both the alternariol 9-O-methyl ether (AME) and the dimethyl sulfoxide (DMSO) molecules exhibit crystallographic mirror symmetry. One of the hydroxy groups makes bifurcated hydrogen bonds, viz. an intramolecular bond with the carbonyl group and an intermolecular bond with the carbonyl group in an inversion-related AME molecule. In the crystal, the AME molecules are organized into stacks parallel with the b axis by [pi]-[pi] interactions between centrosymmetrically related molecules [the distance between the centroid of the central ring and the centroid of the methoxy-substituted benzene ring in the next molecule of the stack is 3.6184 (5) Å]. Pairs of DMSO molecules, linked via centrosymmetric C-H...O contacts, are inserted into the voids created by the AME molecules, making O-H...O and C-H...O contacts with the hosts.

Related literature

For the bioactivity of AME and its precursor alternariol, see: Aly et al. (2008[Aly, A. H., Edrada-Ebel, R., Indrani, I. D., Wray, V., Muller, W. E. G., Totzke, F., Zirrgiebel, U., Schachtele, C., Kubbutat, M. H. G., Lin, W. H., Proksch, P. & Ebel, R. (2008). J. Nat. Prod. 71, 972-980.]); Brugger et al. (2006[Brugger, E.-M., Wagner, J., Schumacher, D. M., Koch, K., Podlech, J., Metzler, M. & Lehmann, L. (2006). Toxicol. Lett. 164, 221-230.]); Pfeiffer et al. (2007[Pfeiffer, E., Schebb, N. H., Podlech, J. & Metzler, M. (2007). Mol. Nutr. Food Res. 51, 307-316.]); Miller et al. (2012[Miller, K. I., Qing, C., Sze, D. M.-Y., Roufogalis, B. D. & Neilan, B. A. (2012). Microb. Ecol. 64, 431-449.]). For their occurrence as contaminants in food and beverages, see: Lau et al. (2003[Lau, B. P.-Y., Scott, P. M., Lewis, D. A., Kanhere, S. R., Cleroux, C. & Roscoe, V. A. (2003). J. Chromatogr. A, 998, 119-131.]). For the related crystal strucutre of alternariol, see: Dasari et al. (2012[Dasari, S., Bhadbhade, M. & Neilan, B. A. (2012). Acta Cryst. E68, o1471.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12O5·C2H6OS

  • Mr = 350.37

  • Monoclinic, C 2/m

  • a = 18.8906 (8) Å

  • b = 6.8391 (3) Å

  • c = 15.3542 (8) Å

  • [beta] = 126.815 (3)°

  • V = 1588.08 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 150 K

  • 0.38 × 0.09 × 0.05 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.916, Tmax = 0.988

  • 7177 measured reflections

  • 1524 independent reflections

  • 1382 reflections with I > 2[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.093

  • S = 1.10

  • 1524 reflections

  • 144 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O1...O1Di 0.80 1.82 2.617 (2) 175
O4-H1O4...O3 0.89 1.76 2.575 (2) 151
O4-H1O4...O3ii 0.89 2.59 3.162 (2) 123
C4-H4C...O1iii 0.93 2.62 3.467 (2) 152
C1D-H4...O4 0.96 2.70 3.401 (2) 130
C1D-H5...O2ii 0.96 2.66 3.2970 (19) 124
Symmetry codes: (i) x, y, z+1; (ii) -x+1, y, -z+1; (iii) -x+1, y, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL-Plus.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2088 ).


Acknowledgements

Funding from the Australian Endeavour Fellowship Scheme (SD) and and the Australian Research Council (BAN) is gratefully acknowledged.

References

Aly, A. H., Edrada-Ebel, R., Indrani, I. D., Wray, V., Muller, W. E. G., Totzke, F., Zirrgiebel, U., Schachtele, C., Kubbutat, M. H. G., Lin, W. H., Proksch, P. & Ebel, R. (2008). J. Nat. Prod. 71, 972-980.  [ISI] [CrossRef] [PubMed] [ChemPort]
Brugger, E.-M., Wagner, J., Schumacher, D. M., Koch, K., Podlech, J., Metzler, M. & Lehmann, L. (2006). Toxicol. Lett. 164, 221-230.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dasari, S., Bhadbhade, M. & Neilan, B. A. (2012). Acta Cryst. E68, o1471.  [CSD] [CrossRef] [details]
Lau, B. P.-Y., Scott, P. M., Lewis, D. A., Kanhere, S. R., Cleroux, C. & Roscoe, V. A. (2003). J. Chromatogr. A, 998, 119-131.  [ISI] [PubMed] [ChemPort]
Miller, K. I., Qing, C., Sze, D. M.-Y., Roufogalis, B. D. & Neilan, B. A. (2012). Microb. Ecol. 64, 431-449.  [ISI] [CrossRef] [PubMed]
Pfeiffer, E., Schebb, N. H., Podlech, J. & Metzler, M. (2007). Mol. Nutr. Food Res. 51, 307-316.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o872-o873   [ doi:10.1107/S1600536813012294 ]

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