title: Crystal structures of three N-(aryl-sulfon-yl)-4-fluoro-benzamides.
abstract: The crystal structures of three N-aryl-sulfonyl-4-fluoro-benzamides, namely 4-fluoro-N-(2-methyl-phenyl-sulfon-yl)benzamide, C14H12FNO3S, (I), N-(2-chloro-phenyl-sulfon-yl)-4-fluorobenzamide, C13H9ClFNO3S, (II), and N-(4-chloro-phenyl-sulfon-yl)-4-fluoro-benzamide monohydrate, C13H9ClFNO3S·H2O, (III), are described and compared with related structures. The asymmetric unit of (I) contains two independent mol-ecules (A and B), while that of (II) contains just one mol-ecule, and that of (III) contains a mol-ecule of water in addition to one main mol-ecule. The dihedral angle between the benzene rings is 82.83 (11)° in mol-ecule A and 85.01 (10)° in mol-ecule 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 mol-ecules, resulting in an R 4 (4)(16) tetra-meric unit. These tetra-meric units are connected into sheets in the bc plane by various C-H⋯O inter-actions, and adjacent sheets are further inter-linked via C-H⋯πar-yl inter-actions, forming a three-dimensional architecture. The crystal structure is further stabilized by πar-yl-πar-yl and S=O⋯πar-yl inter-actions. In the crystal of (II), mol-ecules are connected into R 2 (2)(8) and R 2 (2)(14) dimers via N-H⋯O hydrogen bonds and C-H⋯O inter-actions, respectively; the dimers are further inter-connected via a weak C=O⋯πar-yl inter-action, 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 mol-ecule and the solvent water mol-ecule results in the formation of sheets parallel to the bc plane. The sheets are further connected by C-H⋯O inter-actions and weak C-Cl⋯πar-yl, C-F⋯πar-yl and S=O⋯πar-yl inter-actions, forming a three-dimensional architecture.
authors.affiliation: Department of Chemistry, University College of Science, Tumkur University, Tumkur 572 103, India.
authors.forename: P A
authors.initials: PA
authors.lastname: Suchetan
authors.affiliation: Institution of Excellence, University of Mysore, Manasagangotri, Mysuru-6, India.
authors.forename: S
authors.initials: S
authors.lastname: Naveen
authors.affiliation: Department of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-6, India.
authors.forename: N K
authors.initials: NK
authors.lastname: Lokanath
authors.affiliation: University College of Science, Tumkur, India.
authors.forename: K S
authors.initials: KS
authors.lastname: Srivishnu
authors.affiliation: University College of Science, Tumkur, India.
authors.forename: G M
authors.initials: GM
authors.lastname: Supriya
authors.affiliation: University College of Science, Tumkur, India.
authors.forename: H N
authors.initials: HN
authors.lastname: Lakshmikantha
keywords: C—H⋯O inter­actions; N-(aryl­sulfon­yl)aryl­amides; N—H⋯O hydrogen bonds; O—H⋯O hydrogen bonds; crystal structure