2-[1-(Phenylsulfonyl)ethyl]benzoic acid and 2-[1-(phenylsulfonyl)propyl]benzoic acid

Abstract

In the title acids, C(15)H(14)O(4)S, (I), and C(16)H(16)O(4)S, (II), respectively, the angle between the planes of the benzene ring and the carboxyl group is 13.7 (1) degrees for (I) and 21.3 (1) degrees for (II). The molecular structures are stabilized by intramolecular C-H.O hydrogen bonds. The crystal packing is stabilized by a single O-H.O hydrogen bond in both compounds, in which the O and H atoms are ordered; H.O 1.87 A for (I) and 1.83 A for (II), O.O 2.680 (2) A for (I) and 2.652 (3) A for (II), and O-H.O 172 degrees for (I) and 175 degrees for (II). The hydrogen bond forms a cyclic dimer, with graph-set descriptor R(2)(2)(8), about a centre of symmetry.

2-Benzenesulfonamidobenzoic acid

“…Å is comparable with the reported value of 1.436 (2)Å(Sethu Sankar et al, 2002). The interplanar angle between the phenyl rings in (I) is 89.01 (12)°.…”

“…For background to sulfonamide derivatives, see: Sheppard et al (2006). For similar structures, see: Arshad et al (2009); Sethu Sankar et al (2002); Wijeyesakere et al (2008). For bond-length data, see: Allen et al (1987).…”

2-(4-Bromobenzenesulfonamido)-2-phenylacetic acid monohydrate

“…The S1-N1 distance of 1.617 (6) is shorter than the literature values of 1.6213 (18) Å (Asiri et al, 2009) and 1.6458 (11) Å (Wijeyesakere et al, 2008). The mean S=O distance of 1.439 (5) Å is comparable with the reported value of 1.436 (2) Å (Sethu Sankar et al, 2002). The interplanar angle between the phenyl (C9-C14) and benzene (C1-C6) rings in (I) is 39.5 (5) °.…”

(E)-3-[2-(4-Chlorophenylsulfonyl)vinyl]-6-methyl-4H-chromen-4-one

“…1. It is similar to the structures of the related (Raju et al, 1996), 3-[(2-(Phenylsulfonyl)ethenyl]-4H-1-benzopyran-4-one (IV) (Chen et al, 1996) (Krishnaiah et al, 1995) The mean S═O distance of 1.439 (3) Å is comparable with the reported value of 1.436 (2)Å (Sethu Sankar et al, 2002), and indicates double-bond character of over 60% (Cruickshank, 1961). The C-S distances are slightly different from those in the the related structures (I) -(V).…”

“…For the biological properties of sulfonones and for related structures, see: Alonso et al (2002); Raju et al (1996); ; Mukundam (1990); Krishnaiah et al (1995); Sethu Sankar et al (2002). For bond-length data, see: Allen et al (1987);Sethu Sankar et al (2002). For double-bond character, see: Cruickshank (1961).…”