Research Article: Absolute configuration of micromelin

Date Published: July 01, 2011

Publisher: International Union of Crystallography

Author(s): Hoong-Kun Fun, Ittipon Siridechakorn, Surat Laphookhieo, Suchada Chantrapromma.


The title compound {systematic name: 7-meth­oxy-6-[(1R,2R,5R)-5-methyl-4-oxo-3,6-dioxabicyclo­[3.1.0]hexan-2-yl]-2H-chromen-2-one}, C15H12O6, is a coumarin, which was isolated from the roots of Micromelum glanduliferum. There are two mol­ecules in the asymmetric unit with slight differences in bond angles. In both mol­ecules, the furan ring adopts a flattened envelope conformation. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions into chains along the a axis. Aromatic π–π stacking inter­actions with centroid–centroid distances in the range 3.6995 (11)–3.8069 (11) Å and C⋯O short contacts [3.030 (2)–3.171 (3) Å] also occur.

Partial Text

For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For background to plants in the Rutaceae family, coumarins and their activities, see: Ito et al. (1997 ▶, 2000 ▶); Kamperdick et al. (1999 ▶); Rahmani et al. (2003 ▶); Tangyuenyongwatthana et al. (1992 ▶); Tanti­shaiyakul et al. (1986 ▶); Tanti­vatana et al. (1983 ▶); Thuy et al. (1999 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).




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