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.
Highlights
A novel chalcone, C20H20O, derived from benzylidenetetralone, was synthesized via Claissen–Schmidt condensation between tetralone and 2,4,6-trimethylbenzaldehyde
Molecules are linked by C—HÁ Á ÁO hydrogen bonds, producing R22(20) and R42(12) ring motifs
The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most important contributions for the crystal packing are from HÁ Á ÁH (66.0%), HÁ Á ÁC/ CÁ Á ÁH (22.3%), HÁ Á ÁO/OÁ Á ÁH (9.3%), and CÁ Á ÁC (2.4%) interactions
Summary
Chalcone (systematic name 1,3-diphenyl-2-propene-1-one) is an aromatic ketone that represents the central core for various derivatives with interesting properties, known as chalcones (Kostanecki & Tambor, 1899). Chalcones are found in fruits, vegetables, spices, tea or soy, and find applications as pharmaceuticals (Di Carlo et al, 1999). Chalcones are major intermediates in the synthesis of natural products and are widely used in synthetic and pharmaceutical chemistry (Dhar, 1981; Ansari et al, 2005) because they have antitumor (Modzelewska et al, 2006), antifungal (Lopez et al, 2001), anti-inflammatory (Lee et al, 2006), anti-bacterial (Batovska et al, 2009) or antitubercular properties (Lin et al, 2002). Chalcones consist of two aromatic rings that are linked by a three-carbon ,-unsaturated carbonyl system, leading to a completely delocalized -electron system. As part of our studies in this area, we report the synthesis, crystal structure and Hirshfeld surface analysis of a new chalcone. Symmetry codes: (i) x þ 1; y À 1; z; (ii) Àx À 1; Ày À 1; Àz À 2; (iii) Àx þ 1; Ày; Àz þ 1
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