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

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

Thomas P Mawhinney  1 , Yiyi Li  2 , Deborah L Chance  3 , Steven P Kelley  4 , Valeri V Mossine  1
Affiliations

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

Thomas P Mawhinney et al. Acta Crystallogr E Crystallogr Commun. .

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.

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Figures

Figure 1
Figure 1
Preparation of crystals of (I). (a) Sublimation apparatus used for short-path distillation, (b) Crystals of (R,S)-HMTBA monomer formed on sublimator’s cold finger.
Figure 2
Figure 2
The atomic numbering and displacement ellipsoids at 50% probability level drawn for mol­ecule (I A).
Figure 3
Figure 3
The atomic numbering and displacement ellipsoids at 50% probability level drawn for mol­ecule (I B).
Figure 4
Figure 4
The mol­ecular packing in (I). Color code for crystallographic axes: red − a, green − b, blue − c. Highlighted are hydro­philic regions in the crystal.
Figure 5
Figure 5
Hydrogen bonding in crystal structure of (I). (a) A view of the unit-cell contents shown in projection down the a axis. Hydrogen bonds are shown as cyan dotted lines. (b) Hydrogen-bonding patterns in the crystal structure of (I), as viewed down the a axis.
Figure 6
Figure 6
Views of the Hirshfeld surface for (a) mol­ecule (I A) and (b) mol­ecule (I B), mapped over the d norm in the range 0.7691 to 1.1756 a.u. with the blue-to-red color palette reflecting distances from a point on the surface to the closest nuclei. The mol­ecular fragments involved in the shortest O—H⋯O and C—H⋯O inter­actions are shown.
Figure 7
Figure 7
The two-dimensional fingerprint plots for (a)–(c) mol­ecule (I A) and (d)–(f) mol­ecule (I B), delineated into specific contacts: (a,d) O⋯H/H⋯O (32.3% and 28.5% contribution to the Hirshfeld surfaces of the respective mol­ecules); (b,e) H⋯H (48.9 and 50.4%); (c,f) H⋯S/S⋯H (14.3 and 18.2%).
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References

    1. Alagar, M., Krishnakumar, R. V., Mostad, A. & Natarajan, S. (2005). Acta Cryst. E61, o1165–o1167.
    1. Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
    1. Bhalla, T. C., Kumar, V. & Bhatia, S. K. (2013). Advances in Industrial Biotechnology, edited by R. S. Singh, A. Pandey & C. Larroche, pp. 56–76. Delhi: IK International Publishing House.
    1. Bruker. (2017). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
    1. Busto, E., Richter, N., Grischek, B. & Kroutil, W. (2014). Chem. Eur. J. 20, 11225–11228. - PubMed

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