Crystal structures of three N-(arylsulfonyl)-4-fluorobenzamides

Abstract

The crystal structures of three N-arylsulfonyl-4-fluorobenzamides, namely 4-fluoro-N-(2-methylphenylsulfonyl)benzamide, C14H12FNO3S, (I), N-(2-chlorophenylsulfonyl)-4-fluorobenzamide, C13H9ClFNO3S, (II), and N-(4-chlorophenylsulfonyl)-4-fluorobenzamide monohydrate, C13H9ClFNO3S·H2O, (III), are described and compared with related structures. The asymmetric unit of (I) contains two independent molecules (A and B), 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 molecule A and 85.01 (10)° in molecule B of (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 the A and B molecules, resulting in an R44(16) tetrameric unit. These tetrameric units are connected into sheets in the bc plane by various C—H...O interactions, and adjacent sheets are further interlinked via C—H...πaryl interactions, forming a three-dimensional architecture. The crystal structure is further stabilized by πaryl–πaryl and S=O...πaryl interactions. In the crystal of (II), molecules are connected into R22(8) and R22(14) dimers via N—H...O hydrogen bonds and C—H...O interactions, respectively; the dimers are further interconnected via a weak C=O...πaryl interaction, 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 the bc plane. The sheets are further connected by C—H...O interactions and weak C—Cl...πaryl, C—F...πaryl and S=O...πaryl interactions, forming a three-dimensional architecture.

Keywords

• crystal structure
• N-(arylsulfonyl)arylamides
• N—H...O hydrogen bonds
• O—H...O hydrogen bonds
• C—H...O interactions