Some chalcones derived from thio-phene-3-carbaldehyde: synthesis and crystal structures.

Vu Quoc, Trung, Tran Thi Thuy, Duong, Dang Thanh, Thuan, Phung Ngoc, Thanh, Nguyen Thien, Vuong, Nguyen Thuy, Chinh and Van Meervelt, Luc ORCID: 0000-0003-2186-5209 (2019) Some chalcones derived from thio-phene-3-carbaldehyde: synthesis and crystal structures. Acta crystallographica. Section E, Crystallographic communications, 75 (Pt 7). pp. 957-963.

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Abstract

The synthesis, spectroscopic data and crystal and mol-ecular structures of four 3-(3-phenyl-prop-1-ene-3-one-1-yl)thio-phene derivatives, namely 1-(4-hydroxy-phen-yl)-3-(thio-phen-3-yl)prop-1-en-3-one, C₁₃H₁₀O₂S, (<b>1</b>), 1-(4-meth-oxy-phen-yl)-3-(thio-phen-3-yl)prop-1-en-3-one, C₁₄H₁₂O₂S, (<b>2</b>), 1-(4-eth-oxy-phen-yl)-3-(thio-phen-3-yl)prop-1-en-3-one, C₁₅H₁₄O₂S, (<b>3</b>), and 1-(4--bromophen-yl)-3-(thio-phen-3-yl)prop-1-en-3-one, C₁₃H₉BrOS, (<b>4</b>), are described. The four chalcones have been synthesized by reaction of thio-phene-3-carbaldehyde with an aceto-phenone derivative in an absolute ethanol solution containing potassium hydroxide, and differ in the substituent at the <i>para</i> position of the phenyl ring: -OH for <b>1</b>, -OCH₃ for <b>2</b>, -OCH₂CH₃ for <b>3</b> and -Br for <b>4</b>. The thio-phene ring in <b>4</b> was found to be disordered over two orientations with occupancies 0.702 (4) and 0.298 (4). The configuration about the C=C bond is <i>E</i>. The thio-phene and phenyl rings are inclined by 4.73 (12) for <b>1</b>, 12.36 (11) for <b>2</b>, 17.44 (11) for <b>3</b> and 46.1 (6) and 48.6 (6)° for <b>4</b>, indicating that the -OH derivative is almost planar and the -Br derivative deviates the most from planarity. However, the substituent has no real influence on the bond distances in the α,β-unsaturated carbonyl moiety. The mol-ecular packing of <b>1</b> features chain formation in the <i>a</i>-axis direction by O-H⋯O contacts. In the case of <b>2</b> and <b>3</b>, the packing is characterized by dimer formation through C-H⋯O inter-actions. In addition, C-H⋯π(thio-phene) inter-actions in <b>2</b> and C-H⋯S(thio-phene) inter-actions in <b>3</b> contribute to the three-dimensional architecture. The presence of C-H⋯π(thio-phene) contacts in the crystal of <b>4</b> results in chain formation in the <i>c</i>-axis direction. The Hirshfeld surface analysis shows that for all four derivatives, the highest contribution to surface contacts arises from contacts in which H atoms are involved.

Item Type:	Article
Uncontrolled Keywords:	Hirshfeld analysis, chalcone, crystal structure, thio­phene, α,β-unsaturated carbon­yl
Depositing User:	Symplectic Admin
Date Deposited:	03 Oct 2019 08:58
Last Modified:	19 Jan 2023 00:24
DOI:	10.1107/s2056989019007503
Open Access URL:	https://doi.org/10.1107/S2056989019007503
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3056844