2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry

Caracelli, Ignez and Zukerman-Schpector, Julio and Traesel, Henrique J. and Olivato, Paulo R. and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2019) 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry. Acta Crystallographica Section E Crystallographic Communications, 75 (6). pp. 816-822. ISSN 2056-9890 (In Press)

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Abstract

The title compound, C15H13BrO2S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromophenyl)sulfanyl, benzaldehyde and methoxy residues: crystal symmetry generates a racemic mixture. A twist in the molecule is evident about the methine-C—C(carbonyl) bond as evidenced by the O—C—C—O torsion angle of -20.8 (7)⁰. The dihedral angle between the bromobenzene and phenyl rings is 43.2 (2)⁰, with the former disposed to lie over the oxygen atoms. The most prominent feature of the packing is the formation of helical supramolecular chains as a result of methyland methine-C—H...O(carbonyl) interactions. The chains assemble into a three-dimensional architecture without directional interactions between them. The nature of the weak points of contacts has been probed by a combination of Hirshfeld surface analysis, non-covalent interaction plots and interaction energy calculations. These point to the importance of weaker H...H and C—H...C interactions in the consolidation of the structure.

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