Steric repulsion and supra-molecular assemblies via a two-dimensional plate by C-H?O hydrogen bonds in two closely related 2-(benzo-furan-2-yl)-2-oxoethyl benzoates.

ABSTRACT: 2-(Benzo-furan-2-yl)-2-oxoethyl 2-chloro-benzoate, C17H11ClO4 (I), and 2-(benzo-furan-2-yl)-2-oxoethyl 2-meth-oxy-benzoate, C18H14O5 (II), were synthesized under mild conditions. Their chemical and mol-ecular structures were analyzed by spectroscopic and single-crystal X-ray diffraction studies, respectively. These compounds possess different ortho-substituted functional groups on their phenyl rings, thus experiencing extra steric repulsion force within their mol-ecules as the substituent changes from 2-chloro (I) to 2-meth-oxy (II). The crystal packing of compound (I) depends on weak inter-molecular hydrogen bonds and ?-? inter-actions. Mol-ecules are related by inversion into centrosymmetric dimers via C-H?O hydrogen bonds, and further strengthened by ?-? inter-actions between furan rings. Conversely, mol-ecules in compound (II) are linked into alternating dimeric chains propagating along the [101] direction, which develop into a two-dimensional plate through extensive inter-molecular hydrogen bonds. These plates are further stabilized by ?-? and C-H?? inter-actions.

SUBMITTER: Then LY 

PROVIDER: S-EPMC5598854 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature