Crystal and molecular structure of (5S,8aS,9S)-9-hy­droxy-5-methyl-4,6,7,8,8a,9-hexa­hydro­thieno-[3,2-f] indolizin-5-ium iodide

Viktor Vrábel ^*, Július Sivý ^a, Peter Šafař ^b, Štefan Marchalín ^c

Institute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^a Institute of Mathematics and Physics, Faculty of Mechanical Engineering, Slovak University of Technologyy, Námestie slobody 17, SK-812 31 Bratislava, Slovak Republic
^b Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^c Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic

E-mail: ^* viktor.vrabel@stuba.sk

Abstract: The title compound, C₁₁H₁₆NOS×I, is chiral molecule with three stereogenic centres. The absolute configuration was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine moiety adopts a half-chair conformation with atom displaced by 0.655 (2) Å from the plane of the oder remaining five atoms.The pyrrolidine ring adopts an envelope conformation, with the greatest deviation from the mean plane of the ring being 0.646 (2) Å for the bridge head N atom. The crystal structure of the title compound is stabilized by O—H···I and C—H···O hydrogen bonds.

Keywords: conformation, crystal structure, hydrogenbonds, indolizine, single-crystal X-ray study

Full paper in Portable Document Format: acs_0183.pdf

Acta Chimica Slovaca, Vol. 7, No. 1, 2014, pp. 34—37, DOI: 10.2478/acs-2014-0007

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