Two Related Thienoquinolizidines and Their Crystal, Molecular Structure and Electronic Properties
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, π–π 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.
KeywordsChiral 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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