Crystal structure of (R, S)-2-hy-droxy-4-(methyl-sulfan-yl)butanoic acid

Thomas P Mawhinney; Yiyi Li; Deborah L Chance; Steven P Kelley; Valeri V Mossine

doi:10.1107/S2056989020003138

Crystal structure of (R, S)-2-hy-droxy-4-(methyl-sulfan-yl)butanoic acid

Acta Crystallogr E Crystallogr Commun. 2020 Mar 17;76(Pt 4):562-566. doi: 10.1107/S2056989020003138. eCollection 2020 Apr 1.

Authors

Thomas P Mawhinney¹, Yiyi Li², Deborah L Chance³, Steven P Kelley⁴, Valeri V Mossine¹

Affiliations

¹ Department of Biochemistry, University of Missouri, Columbia, MO 65211, USA.
² Experiment Station Chemical Laboratories, University of Missouri, Columbia, MO 65211, USA.
³ Department of Molecular Microbiology and Immunology, University of Missouri, Columbia, MO 65211, USA.
⁴ Department of Chemistry, University of Missouri, Columbia, MO 65211, USA.

Abstract

The title compound, a major animal feed supplement, abbreviated as HMTBA and alternatively called dl-me-thio-nine hy-droxy analogue, C₅H₁₀O₃S, (I), was isolated in pure anhydrous monomeric form. The melting point is 302.5 K and the compound crystallizes in the monoclinic space group P2₁/c, with two conformationally non-equivalent mol-ecules [(I A ) and (I B )] in the asymmetric unit. The crystal structure is formed by alternating polar and non-polar layers running along the bc plane and features an extensive hydrogen-bonding network within the polar layers. The Hirshfeld surface analysis revealed a significant contribution of non-polar H⋯H and H⋯S inter-actions to the packing forces for both mol-ecules.

Keywords: 2-hydroxy-4-(methylsulfanyl)butanoic acid; CAS 583–91-5; HMTBA; crystal structure; hydrogen bonding; methionine hydroxy analog.

Grants and funding

This work was funded by University of Missouri Agriculture Experiment Station Chemical Laboratories grant . National Institute of Food and Agriculture grant MO-HABC0002.