Crystal structure of (S)- sec-butyl-ammonium l-tartrate monohydrate

Ernlie A Publicover; Jennifer Kolwich; Darcie L Stack; Alyssa J Doué; Kai E O Ylijoki

doi:10.1107/S2056989017005448

Crystal structure of (S)- sec-butyl-ammonium l-tartrate monohydrate

Acta Crystallogr E Crystallogr Commun. 2017 Apr 18;73(Pt 5):716-719. doi: 10.1107/S2056989017005448. eCollection 2017 May 1.

Authors

Ernlie A Publicover¹, Jennifer Kolwich¹, Darcie L Stack¹, Alyssa J Doué¹, Kai E O Ylijoki¹

Affiliation

¹ Department of Chemistry, Saint Mary's University, 923 Robie St., Halifax, NS, B3H 3C3, Canada.

Abstract

The title hydrated mol-ecular salt, C₄H₁₂N⁺·C₄H₅O₆^-·H₂O, was prepared by deprotonation of enanti-opure l-tartaric acid with racemic sec-butyl-amine in water. Only one enanti-omer was observed crystallographically, resulting from the combination of (S)-sec-butyl-amine with l-tartaric acid. The sec-butyl-ammonium moiety is disordered over two conformations related by rotation around the CH-CH₂ bond; the refined occupancy ratio is 0.68 (1):0.32 (1). In the crystal, mol-ecules are linked through a network of O-H⋯O and N-H⋯O hydrogen-bonding inter-actions, between the ammonium H atoms, the tartrate hy-droxy H atoms, and the inter-stitial water, forming a three-dimensional supra-molecular structure.

Keywords: chiral resolution; crystal structure; hydrogen bonding; l-tartaric acid; monohydrate; sec-butylamine.