Crystal structures of threeN-(arylsulfonyl)-4-fluorobenzamides

Abstract

The crystal structures of threeN-arylsulfonyl-4-fluorobenzamides, namely 4-fluoro-N-(2-methylphenylsulfonyl)benzamide, C14H12FNO3S, (I),N-(2-chlorophenylsulfonyl)-4-fluorobenzamide, C13H9ClFNO3S, (II), andN-(4-chlorophenylsulfonyl)-4-fluorobenzamide monohydrate, C13H9ClFNO3S·H2O, (III), are described and compared with related structures. The asymmetric unit of (I) contains two independent molecules (AandB), while that of (II) contains just one molecule, and that of (III) contains a molecule of water in addition to one main molecule. The dihedral angle between the benzene rings is 82.83 (11)° in moleculeAand 85.01 (10)° in moleculeBof (I), compared to 89.91 (10)° in (II) and 81.82 (11)° in (III). The crystal structure of (I) features strong N—H...O hydrogen bonds between theAandBmolecules, resulting in anR44(16) tetrameric unit. These tetrameric units are connected into sheets in thebcplane by various C—H...O interactions, and adjacent sheets are further interlinkedviaC—H...πarylinteractions, forming a three-dimensional architecture. The crystal structure is further stabilized by πaryl–πaryland S=O...πarylinteractions. In the crystal of (II), molecules are connected intoR22(8) andR22(14) dimersviaN—H...O hydrogen bonds and C—H...O interactions, respectively; the dimers are further interconnectedviaa weak C=O...πarylinteraction, leading to the formation of chains along [1-10]. In the crystal of (III), N—H...O and O—H...O hydrogen bonds involving both the main molecule and the solvent water molecule results in the formation of sheets parallel to thebcplane. The sheets are further connected by C—H...O interactions and weak C—Cl...πaryl, C—F...πaryland S=O...πarylinteractions, forming a three-dimensional architecture.