Crystal, molecular and electron structure of (2R,3R,4aS,5S,7R,10aS,10bS)-5-ethyl-2,3-dimethoxy- 2,3,7-trimethyl-decahydro-2H-[1,4]dioxino[2,3-g]indolizin- 7-ium iodide hydrate

Viktor Vrábel ^*, Július Sivý ^a, Peter Šafař ^b

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 Technology, 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

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

Abstract: The title compound, C₁₇H₃₂NO₄I·H₂O, is chiral molecule with seven 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 and 1,4-dioxane ring adopt a chair conformation, with two atoms displaced by –0.530(3), 0.712(3) and –0.631(2), 0.602(2) Å, respectively, from the plane of the other four atoms. The conformation of the pyrrolidine ring is close to that of a envelope, with the flap atom displaced by –0.600(3) Å from the plane through the remaining four atoms. The electron structure was calculated by the semiempirical quantum chemistry method PM3. The crystal structure of compound is stabilized by O—H···I and O—H···O hydrogen bonds.

Keywords: conformation, crystal and electron structure, hydrogen bonds, indolizine, single-crystal X-ray study

Full paper in Portable Document Format: acs_0162.pdf

Acta Chimica Slovaca, Vol. 6, No. 2, 2013, pp. 173—176, DOI: 10.2478/acs-2013-0027

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