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. 2019 May 10;75(Pt 6):746-750.
doi: 10.1107/S2056989019006182. eCollection 2019 Jun 1.

Crystal structure and Hirshfeld surface analysis of (E)-2-(2,4,6-tri-methyl-benzyl-idene)-3,4-di-hydro-naphthalen-1(2 H)-one

Cemile Baydere  1 , Merve Taşçı  2 , Necmi Dege  1 , Mustafa Arslan  2 , Yusuf Atalay  2 , Irina A Golenya  3
Affiliations

Crystal structure and Hirshfeld surface analysis of (E)-2-(2,4,6-tri-methyl-benzyl-idene)-3,4-di-hydro-naphthalen-1(2 H)-one

Cemile Baydere et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

A novel chalcone, C20H20O, derived from benzyl-idene-tetra-lone, was synthesized via Claissen-Schmidt condensation between tetra-lone and 2,4,6-tri-methyl-benzaldehyde. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, producing R 2 2(20) and R 2 4(12) ring motifs. In addition, weak C-H⋯π and π-stacking inter-actions are observed. The inter-molecular inter-actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most important contributions for the crystal packing are from H⋯H (66.0%), H⋯C/ C⋯H (22.3%), H⋯O/O⋯H (9.3%), and C⋯C (2.4%) inter-actions. Shape-index plots show π-π stacking inter-actions and the curvedness plots show flat surface patches characteristic of planar stacking.

Keywords: Hirshfeld surface analysis; chalcone; crystal structure; hydrogen bond.

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Figures

Figure 1
Figure 1
The mol­ecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Figure 2
A view along the a axis of the title structure. Blue dashed lines denote the C—H⋯O hydrogen bonds which form formula image(20) and formula image(12) ring motifs. C—H⋯π inter­actions are shown as green dashes lines.
Figure 3
Figure 3
(a) dnorm mapped on Hirshfeld surfaces for visualizing the inter­molecular inter­actions; (b) shape-index map and (c) curvedness map of the title compound.
Figure 4
Figure 4
dnorm mapped on Hirshfeld surfaces for visualizing the inter­molecular inter­actions.
Figure 5
Figure 5
(a) The overall two-dimensional fingerprint plot and (b) Hirshfeld surface representations with the function d norm plotted onto the surface for (i) H⋯H, (ii) H⋯C/C⋯H, (iii) H⋯O/O⋯H and (iv) C⋯C inter­actions. (c) The two-dimensional fingerprint plots for the title compound, delineated into (i) H⋯H, (ii) H⋯C/ C⋯H, (iii) H⋯O/O⋯H, (iv) C⋯C inter­actions.
See this image and copyright information in PMC

References

    1. Ansari, F. L., Nazir, S., Noureen, H. & Mirza, B. (2005). Chem. Biodivers. 2, 1656–1664. - PubMed
    1. Baddeley, T. C., Gomes, L. R., Low, J. N., Turner, A. B., Wardell, J. L. & Watson, G. J. R. (2017). Z. Kristallogr. 232, 317–333.
    1. Batovska, D., Parushev, S., Stamboliyska, B., Tsvetkova, I., Ninova, M. & Najdenski, H. (2009). Eur. J. Med. Chem. 44, 2211–2218. - PubMed
    1. Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: Wiley.
    1. Di Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Sci. 65, 337–353. - PubMed

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