Abstract
The title compound, C15H13ClO2S, comprises (4-chloro-phen-yl)sulfanyl, benzaldehyde and meth-oxy residues linked at a chiral methine-C atom (the crystal is racemic). A twist in the methine-C-C(carbon-yl) bond [O-C-C-O torsion angle = 19.3 (7)°] leads to a dihedral angle of 22.2 (5)° between the benzaldehyde and methine+meth-oxy residues. The chloro-benzene ring is folded to lie over the O atoms, with the dihedral angle between the benzene rings being 42.9 (2)°. In the crystal, the carbonyl-O atom accepts two C-H⋯O inter-actions with methyl- and methine-C-H atoms being the donors. The result is an helical supra-molecular chain aligned along the c axis; chains pack with no directional inter-actions between them. An analysis of the Hirshfeld surface points to the important contributions of weak H⋯H and C⋯C contacts to the mol-ecular packing.
Highlights
The title compound, C15H13ClO2S, comprises (4-chlorophenyl)sulfanyl, benzaldehyde and methoxy residues linked at a chiral methine-C atom
The chlorobenzene ring is folded to lie over the O atoms, with the dihedral angle between the benzene rings being 42.9 (2)
The result is an helical supramolecular chain aligned along the c axis; chains pack with no directional interactions between them
Summary
As part of our ongoing studies on the conformational and electronic characteristics of some -thiocarbonyl, -bis-thiocarbonyl and -thio- -oxacarbonyl compounds, e.g. N,Ndiethyl-2-[(40-substituted)phenylthio]acetamides (Vinhato et al, 2013), 1-methyl-3-phenylsulfonyl-2-piperidones (Zukerman-Schpector et al, 2008), 3,3-bis[(40-substituted) phenylsulfanyl]-1-methyl-2-piperidones (Olivato et al, 2013), 2alkylthio-2-alkylsulfinyl-acetophenones and 2-alkylthio-2phenylsulfonyl-acetophenones, 2-alkylsulfinyl-2-alkylsulfonylacetophenones (Distefano et al, 1996), 2-methoxy-2-[(40substituted) phenylsulfanyl]-acetophenones (ZukermanSchpector et al, 2015; Caracelli et al, 2015) and 2-methoxy-2(phenylselanyl)-(40-substituted)acetophenones (Traesel et al, 2018), utilizing infrared spectroscopy, computational chemistry and X-ray diffraction methods, the title compound (I) was synthesized and characterized. The primary motivation behind this work is the search for selenium/sulfur-containing compounds with anti-inflammatory activity that could be selective COX-2 inhibitors (Cerqueira et al, 2015, 2017). Molecular docking studies have been conducted in order to understand the mechanism of inhibition (Baptistini, 2015). The crystal and molecular structures of (I) are described along with an analysis of the calculated Hirshfeld surfaces and non-covalent interaction plots for selected interactions. C8—C9 bond as seen in the value of the O1—C8—C9—O2 torsion angle of 19.3 (7). The 4-chlorophenyl group is orientated so that the ring lies over the oxygen atoms with the dihedral angle between the benzene rings being 42.9 (2)
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