Isochroman derivatives and their tendency to crystallize in chiral space groups
In methyl [5-methoxy-4-(4-methoxyphenyl)isochroman-3-yl]acetate, C20H22O5, (I), and methyl [4-(2,5-dimethoxyphenyl)-8-methoxyisochroman-3-yl]acetate, C21H24O6, (II), the heterocyclic rings adopt half-chair conformations. The substituents at the 3- and 4-positions are in a trans configuration in both (I) and (II), being in an axial conformation in (I) and in an equatorial conformation in (II). The crystal structure of (I) is stabilized by weak C—H…O hydrogen bonding, leading to the formation of an infinite three-dimensional network. Compound (II) crystallizes in a chiral space group. This feature, which was also found in previously investigated isochroman derivatives, is related to the arrangement of substituents attached to the isochroman moiety.
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Document Type: Research Article
Publication date: 2004-04-01