Crystal and molecular structure of (9aS,10S)-6-Oxo-6,7,8,9,9a,10-hexahydro-4H-thieno--[2,3-b]quinolizin-10-yl acetate
Vrábel Viktor *, Sivý Július a, Šafař Peter b, Štefan Marchalín c
Institute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak Technical Uni-versity,
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
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, C13H15NO3S, is a chiral molecule with two stereogenic centres. Its absolute configuration was derrived from the synthesis and confirmed by structure determination. The expected stereochemistry of atoms C5 and C6 was confirmed to be S. The central N-heterocyclic rings are not planar and adopt a half-chair conformation. A calculation of least-squares planes showed that these rings are puckered in such a manner that the five atoms C1, C2, C3, C5 and N1 (second ring: N1, C6, C7, C10 and C11) are planar, while atoms C4 (C5) are displaced from these planes with the out-of-plane displacement of 0.582 (3) Å and 0,666 (2) Å in the second ring, respectively. Dihedral angle between the planes of the central N-heterocyclic rings is 40.0 (1)°. Crystal structure is stabilized by C—H···O hydrogen interactions.
Keywords: crystal structure, hydrogen interactions, quinolizine, single-crystal X-ray study
Full paper in Portable Document Format: acs_0261.pdf
Acta Chimica Slovaca, Vol. 9, No. 2, 2016, pp. 180—183, DOI: 10.1515/acs-2016-0030