Crystal, molecular and electronic structure of (5S,11R,11aS)-11-hydroxy-5-methyl-1,2,3,4,5,6,11,11a-octahydropyrido[1,2-b]isoquinolin-5-ium iodide

Július Sivý ^*, Peter Šafář ^a, Jozefína Žúžiová ^b

Faculty of Mechanical Engineering, Slovak University of Technology, Námestie slobody 17, SK-812 31 Bratislava, Slovak Republic
^a Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 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: ^* julius.sivy@stuba.sk

Abstract: The title compound, C₁₄H₂₀INO, is a molecule with three stereogenic centres. It absolute configuration was derived from the synthesis and confirmed by structure determination (AD, Flack (Parsons’) parameter: 0.031 (8)). The expected stereochemistry of atoms N1 was confirmed to be S, C5 was confirmed to S, C6 was confirmed to R. The central N-heterocyclic ring is not planar and adopts a half-chair conformation. A calculation of least-squares planes showed that these rings are puckered in such a manner that the five atoms: C5, C6, C7, C12 and C13 (the second ring: C1, C2, C3, C4, C5 and N1) are planar, while atom N1 is displaced from these plane with the out-of-plane displacement of –0.694 (4) and –0.670 (5) Å in the second ring, respectively. Dihedral angle between the planes of the central N-heterocyclic rings is 23.4 (2)°. Crystal structure is also stabilized by C—H···O hydrogen interactions.

Keywords: crystal structure, DFT calculation, hydrogen interactions, isoquinoline, single-crystal X-ray study

Full paper in Portable Document Format: acs_0305.pdf

Acta Chimica Slovaca, Vol. 11, No. 2, 2018, pp. 94—98, DOI: 10.2478/acs-2018-0014

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