Crystal structures of threeN-aryl-2,2,2-tribromoacetamides

Abstract

ThreeN-aryl-2,2,2-tribromoacetamides, namely, 2,2,2-tribromo-N-(2-fluorophenyl)acetamide, C8H5Br3FNO, (I), 2,2,2-tribromo-N-[3-(trifluoromethyl)phenyl]acetamide, C9H5Br3F3NO, (II) and 2,2,2-tribromo-N-(4-fluorophenyl)acetamide, C8H5Br3FNO, (III) were synthesized and their crystal structures were analysed. In the crystal structure of (I), C—Br...πarylinteractions connect the molecules into dimers, which in turn are connectedviaBr...Br contacts [3.6519 (12) Å], leading to the formation of a one-dimensional ladder-type architecture. The crystal structure of (II) features chains linked by N—H...O and C—H...O hydrogen bonds. Two such chains are interlinked to form ribbons through Br...Br [3.6589 (1) Å] and Br...F [3.0290 (1) Å] interactions. C—Br...πaryland C—F...πarylinteractions between the ribbons extend the supramolecular architecture of (II) from one dimension to two. In (III), the molecules are connected intoR22(8) dimersviapairs of C—H...F interactions and these dimers form ribbons through Br...Br [3.5253 (1) Å] contacts. The ribbons are further interlinked into columnsviaC—Br...O=C contacts, forming a two-dimensional architecture.