Received 14 January 2013
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 - 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-HO contacts, are inserted into the voids created by the AME molecules, making O-HO and C-HO contacts with the hosts.
For the bioactivity of AME and its precursor alternariol, see: Aly et al. (2008); Brugger et al. (2006); Pfeiffer et al. (2007); Miller et al. (2012). For their occurrence as contaminants in food and beverages, see: Lau et al. (2003). For the related crystal strucutre of alternariol, see: Dasari et al. (2012).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); 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 ).
Funding from the Australian Endeavour Fellowship Scheme (SD) and and the Australian Research Council (BAN) is gratefully acknowledged.
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