Crystal structures of the diastereomeric salt pair of the prostaglandin intermediate 1R, 2S(+)-cis-2-hydroxycyclopent-4-enylacetic acid with S- and R- 1-phenylethylamine

Mátyás Czugler, Ingeborg Csöregh, Alajos Kálmán, Ferenc Faigl, Mária Ács

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Abstract

Crystal structures of an enantiomeric salt pair formed between 1R,2S-cis-2-hydroxycyclopent-4-enylacetic acid (S-HCA) and R(+)-1-phenylethylamine (R-PEA) and the corresponding S-PEA salt have been determined by X-ray crystallography. The S-HCA:R-PEA 1:1 salt (R-HCA-PEA hereafter) is orthorhombic, P212121, with the unit-cell parameters a = 5.806(1), b = 9.261(1), c = 27.624(2) Å and R = 0.056 for 1162 reflections at ambient temperature. The S-HCA:S-PEA 1:1 salt (S-HCAPEA) is also orthorhombic, P212121, with the unit-cell data a = 6.034(2), b = 11.840(7), c = 20.198(11) Å at 170 K, R = 0.082 for 1196 data measured at low temperatures (170 K). The R-HCAPEA salt has its two components assembled into an elongated rod-like shape via two-dimensional hydrogen bonding between cations and anions thus forming a well-ordered crystal. In contrast, the cation and anion in the S-HCAPEA salt forms a more globular aggregate and displays orientation disorder in the five-membered ring part of the anion and maintains an essentially one-dimensional hydrogen-bond network, while the total number of hydrogen bonds between cationic and anionic species remains three in both crystals.

Original languageEnglish
Pages (from-to)157-170
Number of pages14
JournalJournal of Molecular Structure
Volume196
Issue numberC
DOIs
Publication statusPublished - May 1989

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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