1369788-12-4Relevant articles and documents
Structural study of three o-hydroxyacetophenone derivatives using X-ray powder diffraction: Interplay of weak intermolecular interactions
Chattopadhyay, Basab,Ghosh, Soumen,Mondal, Swastik,Mukherjee, Monika,Mukherjee, Alok K.
, p. 837 - 846 (2012)
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-(α-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 34.9°. The crystal packing in the compounds is stabilized by an interplay of weak hydrogen bonds, such as C-H...O, C-H...π and π...π interactions, forming supramolecular assemblies. The intermolecular C-H...O hydrogen bonds in 1-3 generate C11(6) chains and Rmn(X) rings, which are further connected through C-H...π hydrogen bonds and π...π 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.
