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Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitro-phen-yl)prop-2-en-1-one.

ABSTRACT: The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethyl-ene C=C and carbonyl C=O double bonds in the enone unit. The mol-ecule is significantly twisted with a dihedral angle of 48.63?(14)° between the anthracene ring system and the benzene ring. In the crystal, mol-ecules are linked into inversion dimers with an R 2 2(10) graph-set motif via pairs of C-H?O hydrogen bonds. The inter-molecular inter-actions were analysed and qu-anti-fied by Hirshfeld surface analysis. The mol-ecular structure was optimized and a small HOMO-LUMO energy gap of 2.55?eV was obtained using the DFT method at the B3LYP/6-311?G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52?eV obtained from the UV-vis analysis. The crystal used was a two-component merohedral twin with a refined ratio of 0.1996?(16):0.8004?(16).

SUBMITTER: Zaini MF 

PROVIDER: S-EPMC6505597 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Crystal structure and optical properties of fused-ring chalcone (<i>E</i>)-3-(anthracen-9-yl)-1-(4-nitro-phen-yl)prop-2-en-1-one.

Zaini Muhamad Fikri MF   Razak Ibrahim Abdul IA   Khairul Wan Mohd WM   Arshad Suhana S  

Acta crystallographica. Section E, Crystallographic communications 20190425 Pt 5

The title compound, C<sub>23</sub>H<sub>15</sub>NO<sub>3</sub>, adopts an <i>s-cis</i> conformation with respect to the ethyl-ene C=C and carbonyl C=O double bonds in the enone unit. The mol-ecule is significantly twisted with a dihedral angle of 48.63 (14)° between the anthracene ring system and the benzene ring. In the crystal, mol-ecules are linked into inversion dimers with an <i>R</i> <sub>2</sub> <sup>2</sup>(10) graph-set motif <i>via</i> pairs of C-H⋯O hydrogen bonds. The inter-molecular  ...[more]

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