Open AccessSupramolecular structures of three configurational isomers of 1‐phenylethanaminium malate(1–)
Author(s) -
Turkington David E.,
Ferguson George,
Lough Alan J.,
Glidewell Christopher
Publication year - 2004
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270104015793
Subject(s) - hydrogen bond , chemistry , crystallography , ion , supramolecular chemistry , stereochemistry , crystallization , enantiomer , salt (chemistry) , crystal structure , molecule , organic chemistry
In rac ‐1‐phenylethanaminium rac ‐malate(1−), C 8 H 12 N + ·C 4 H 5 O 5 − , (I), the anions are linked by two inter‐anion O—H⋯O hydrogen bonds into sheets generated by a glide plane and hence containing both enantiomers of the anion. The cations are linked to the anion sheets by three N—H⋯O hydrogen bonds, such that cations of R configuration are bonded to one face of the sheet and cations of S configuration are bonded to the other face. In ( R )‐1‐phenylethanaminium ( S )‐malate(1−), C 8 H 12 N + ·C 4 H 5 O 5 − , (III), the anions are again linked by two O—H⋯O hydrogen bonds, in one of which the H atom is disordered over two sites, into sheets very similar to those in (I) but which are generated in (III) by translation and so contain only a single enantiomer. The cations in (III) are linked to the anion sheets by three N—H⋯O hydrogen bonds, but the cations are bonded to only one face of the anion sheet. Co‐crystallization of ( R )‐1‐phenylethanamine with rac ‐malic acid gives the salt ( R )‐1‐phenylethanaminium malate(1−) C 8 H 12 N + ·C 4 H 5 O 5 − , (II), with a structure very similar to that of (III) but where only ca 75% of the anion sites are occupied by ( S )‐malate(1−), with the remaining 25% occupied by ( R )‐malate(1−). The layers in (II) show a significant displacement along the [001] direction compared with those in (III).