C-H...O, C-H...π and π-π Interactions in Three Benzofuran-2-yl Ketone Derivatives

Abstract

The molecules of 2-benzoyl-1-benzofuran, C<inf>15</inf>H<inf>10</inf>O <inf>2</inf>, (I), interact through double C-H⋯O hydrogen bonds, forming dimers that are further linked by C-H⋯O, C-H⋯π and π-π interactions, resulting in a three-dimensional supramolecular network. The dihedral angle between the benzoyl and benzofuran fragments in (I) is 46.15 (3)°. The molecules of bis(5-bromo-1-benzofuran-2-yl) ketone, C <inf>17</inf>H<inf>8</inf>Br<inf>2</inf>O<inf>3</inf>, (II), exhibit C <inf>2</inf> symmetry, with the carbonyl group (C=O) lying along the twofold rotation axis, and are linked by a combination of C-H⋯O and C-H⋯π interactions and Br⋯Br contacts to form sheets. The stability of the molecular packing in 3-mesityl-3-methylcyclobutyl 3-methylnaphtho[1,2-b]furan-2-yl ketone, C<inf>28</inf>H<inf>28</inf>O <inf>2</inf>, (III), arises from C-H⋯π and π-π stacking interactions. The fused naphthofuran moiety in (III) is essentially planar and makes a dihedral angle of 81.61 (3)° with the mean plane of the trimethylbenzene ring. © 2005 International Union of Crystallography.