Journal of Chemical Crystallography

, Volume 49, Issue 3, pp 174–180 | Cite as

Two Related Thienoquinolizidines and Their Crystal, Molecular Structure and Electronic Properties

  • Július SivýEmail author
  • Štefan Marchalín
  • Peter Šafář
Original Paper


Two crystals of quinolizidine compounds; systematic name: (rac)-(7,8,9,9a)-tetrahydro-4H-thieno[2,3-b]quinolizine-6,10-dione, (I), and (rac)-(9a,10)-10-hydroxy-8,9,9a,10-tetrahydro-4H-thieno[2,3-b]quinolizin-6(7H)-one, (II), have been compared and characterized by single-crystal X-ray diffraction and electronic analysis. N-heterocyclic rings in both structures are not planar and adopt a half-chair conformation. The molecules of (I) are linked via weak C–H···O hydrogen bonds into chains along c axis. While the crystal stacks in compound (II) are formed by strong O–H···O hydrogen bonds the molecules link into infinite zig-zag chains along the b axis. In both crystal structures, ππ stacking and C–H···π interactions are also observed. Calculation of the net atomic charges shows that O atoms in both compounds carry a relatively large negative charges, in comparison with the corresponding H atoms. Crystal, molecular and electronic structures of these compounds, which are influenced by hydrogen-bonded assemblies in the molecular crystals, are discussed in detail.

Graphical Abstract

Crystal, molecular and electronic structures of two related tricyclic compounds containing thienoquinolizidine ring skeleton, both structures have similar quinolizine ring moieties assuming conformations resembling half-chair.


Chiral compounds Quinolizine derivatives Racemic mixture X-ray structure determination Ab initio calculations DFT/B3LYP/6-311G/Auto 



This work was supported by the Slovak Research and Development Agency under the contract no. APVV-17-0513 and by the Scientific Grant Agency of the Slovak Republic VEGA (Project No. 1/0262/19). This contribution is also the result of the project: Research Center for Industrial Synthesis of Drugs, ITMS 26240220061, supported by the Research & Development Operational Program funded by the ERDF. We are grateful to the HPC centre at the Slovak University of Technology in Bratislava, which is a part of the Slovak Infrastructure of High Performance Computing (SIVVP project, ITMS code 26230120002, funded by the European region development funds, ERDF), for the computational time and the resources.


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Authors and Affiliations

  1. 1.Faculty of Mechanical EngineeringSlovak University of TechnologyBratislavaSlovak Republic
  2. 2.Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food TechnologySlovak University of TechnologyBratislavaSlovak Republic

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