Structural study of three o-hydroxyacetophenone derivatives using X-ray powder diffraction : interplay of weak intermolecular interactions

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Chattopadhyay, Basab ; Ghosh, Soumen ; Mondal, Swastik ; Mukherjee, Monika ; Mukherjee, Alok K.:
Structural study of three o-hydroxyacetophenone derivatives using X-ray powder diffraction : interplay of weak intermolecular interactions.
In: CrystEngComm. Bd. 14 (2012) . - S. 837-846.
ISSN 1466-8033
DOI: https://doi.org/10.1039/C1CE05920C

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Abstract

A family of three o-hydroxyacetophenone derivatives, 2-hydroxy-5-methoxy-4-methylacetophenone (1), 5-methoxy-4-methyl-2-(phenylmethoxy)acetophenone (2) and 2-O-(small alpha-methyl carboethoxy)-5-methoxy-4-methyl-acetophenone (3) were synthesized and their crystal structures were solved using laboratory X-ray powder diffraction data along with a detailed analysis of the Hirshfeld surfaces and 2D-fingerprint plots{,} facilitating a comparison of intermolecular interactions. The DFT optimized molecular geometries in 1 and 3 agree closely with those obtained from the crystallographic studies. In 2{,} however{,} the relative orientation of the two planar phenyl rings as established by the X-ray analysis and quantum mechanical calculations differs by 34.9degree. The crystal packing in the compounds is stabilized by an interplay of weak hydrogen bonds{,} such as C-HO{,} C-Hsmall pi and small pismall pi interactions{,} forming supramolecular assemblies. The intermolecular C-HO hydrogen bonds in 1-3 generate C11(6) chains and Rmn(X) rings{,} which are further connected through C-Hsmall pi hydrogen bonds and small pismall pi interactions to produce parallel molecular sheets built by fused R22(24) rings in 1{,} a three-dimensional architecture with C22(16)R22(6)R22(14) synthons in 2{,} and a two-dimensional columnar framework in 3.