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

The crystal structures of three N-aryl­sulfonyl-4-fluoro­benzamides, namely 4-fluoro-N-(2-methyl­phenyl­sulfon­yl)benzamide, C(14)H(12)FNO(3)S, (I), N-(2-chloro­phenyl­sulfon­yl)-4-fluorobenzamide, C(13)H(9)ClFNO(3)S, (II), and N-(4-chloro­phenyl­sulfon­yl)-4-fluoro­benzamide monohydrate, C(13)H(9)ClFNO(3)S·H(2)O, (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 R (4) (4)(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⋯π(ar­yl) inter­actions, forming a three-dimensional architecture. The crystal structure is further stabilized by π(ar­yl)–π(ar­yl) and S=O⋯π(ar­yl) inter­actions. In the crystal of (II), mol­ecules are connected into R (2) (2)(8) and R (2) (2)(14) dimers via N—H⋯O hydrogen bonds and C—H⋯O inter­actions, respectively; the dimers are further inter­connected via a weak C=O⋯π(ar­yl) 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⋯π(ar­yl), C—F⋯π(ar­yl) and S=O⋯π(ar­yl) inter­actions, forming a three-dimensional architecture.