Research Article: 5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione

Date Published: July 01, 2012

Publisher: International Union of Crystallography

Author(s): Shailesh K. Goswami, Lyall R. Hanton, C. John McAdam, Stephen C. Moratti, Jim Simpson.


The title mol­ecule, C14H14O4, lies on a twofold rotation axis that bis­ects the central benzene ring, with only one half-mol­ecule in the asymmetric unit. The pyran­one systems adopt distorted twist- boat conformations, with the two methyl­ene C atoms displaced by 0.537 (1) and 0.163 (2) Å from the best-fit plane through the remaining five C and O atoms (r.m.s. deviation = 0.073 Å). In the crystal, bifurcated C—H⋯(O,O) hydrogen bonds link pairs of adjacent mol­ecules in an obverse fashion, stacking mol­ecules along c. These contacts are further stabilized by very weak π–π inter­actions between adjacent benzene rings with centroid–centroid distances of 4.1951 (4) Å. Additional C—H⋯O contacts link these stacks, giving a three-dimensional network.

Partial Text

For the synthesis, see: Lecea et al. (2010 ▶). For details of the Cambridge Structural Database, see: Allen (2002 ▶) and for related structures, see: Cameron et al. (2011 ▶); Goswami et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).




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