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[(2R,5R,6S,9R)-6-Isopropyl-9-methyl-1,4-dioxaspiro-[4.5]decan-2-yl]methyl 4-bromo-benzoate.

ABSTRACT: The title compound, C(20)H(27)BrO(4), a 4-bromo-benzoyl derivative of a stereoisomer of glycerol menthonide, synthesized as part of a study of 3-carbon stereochemical moieties, crystallizes with two crystallographically independent mol-ecules in the asymmetric unit, the two mol-ecules differing only in one of the C-O-C-C torsion angles around the ester O atom [-106.5 (7) and 146.1 (6)°]. The two mol-ecules are crystallographically related by a pseudotranslation along the (011) diagonal of the unit cell, emulating a primitive monoclinic cell of half the volume. The translational symmetry is broken by the 4-bromo-benzoate groups. The crystallographic assignment of the absolute stereochemistry is consistent with having started with (-)-menthone, the acetal C atom is R and the secondary alcohol is R. This brings the bromo-benzoate into approximately the same plane as the menthyl ring and cis to the isopropyl group. The glycerol menthonide sections of the molecules interact with each other via C-H⋯O interactions, leading to the formation of chains either A or B molecules that stretch parallel to [010], forming column-shaped double chains. Interactions between neighboring columns are limited to van der Waals contacts.

SUBMITTER: Kiessling A

PROVIDER: S-EPMC3051951 | biostudies-literature |

REPOSITORIES: biostudies-literature

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