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A comparative study of X-ray structural analysis, DFT computations, and Hirshfeld surface analysis for decahydroacridine-1,8-diones

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Abstract

Crystal structure analysis and DFT computational calculation of two symmetrical and unsymmetrical decahydroacridine-1,8-diones (DHACs) were carried out to elucidate the effect of the aryl-substituted heterocyclic core in these compounds on the comparative bond lengths, bond, and dihedral angles. According to these findings, the central heterocyclic ring in these compounds is exhibited in the pseudo-boat conformation, in which the aryl substitution occupies the pseudo-axial position. Moreover, the fused outer rings were in the twisted half-chair conformation. The weak and strong inter- and intramolecular interactions between the suitable donor–acceptor positions (N‒H···O, C‒H···O, H‒N···H and C‒H···π of the C=C double bond) in symmetrical and enantiomeric pairs of unsymmetrical DHACs affect the orientation of the molecules in the crystal packing. The relative contributions of various intermolecular interactions in these compounds are evaluated using Hirshfeld surface analysis. The DFT calculations were performed to outline the optimized structure, molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs), natural bond orbital (NBO) and to elucidate the effect of the space orientation of the attached aryl ring toward the heterocyclic ring on the total energy content of DHAC 2. Additionally, MEP analysis in DHAC 2 revealed that the negative electrostatic potential is more concentrated around the O1-atom of the C1=O1 double bond than the O2-atom of the C13=O2 double bond. The results of the NBO analysis demonstrated that in the crystal packing of compounds 1 and 2 the strongest intermolecular interaction occurs from the LP(2)O2 to σ*(N1–H) and LP(1)O1 to σ*(N1‒H), respectively.

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Acknowledgements

We acknowledge the Research Council and Office of Graduate Studies of the University of Isfahan for financial support. We would like also to thank Professor Hassan Sabzyan for the helpful discussion.

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Authors and Affiliations

  1. Department of Chemistry, University of Isfahan, Isfahan, 81746-73441, Iran

    Fatemeh S. Hosseininasab, Hamid R. Memarian & Hadi Amiri Rudbari

  2. Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057, Zurich, Switzerland

    Olivier Blacque

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  1. Fatemeh S. Hosseininasab
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H. R. Memarian has defined the research project and designed the experiments and computational tasks and supervised the whole research and also contributed to all discussions and preparation and finalization of the manuscript and its sequential upgrade and revisions. F. Hosseininasab has carried out all experiments and computations, and contributed to all discussions and preparation and finalization of the manuscript and its subsequent versions. H. Amiri Rudbari and O. Blacque have carried out the single crystal structure analysis and contributed to the relevant discussions.

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Correspondence to Hamid R. Memarian.

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Appendix A

Appendix A

The crystallographic data are deposited, and CCDC 2298667 and CCDC 2166749 contain the supplementary crystallographic data for compounds 1 and 2. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html

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Hosseininasab, F.S., Memarian, H.R., Rudbari, H.A. et al. A comparative study of X-ray structural analysis, DFT computations, and Hirshfeld surface analysis for decahydroacridine-1,8-diones. J IRAN CHEM SOC 21, 1997–2015 (2024). https://doi.org/10.1007/s13738-024-03045-3

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