2-(Benzenesulfonamido)acetic acid

Abstract

Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.004 Å; R factor = 0.043; wR factor = 0.116; data-to-parameter ratio = 18.1.The title compound, C 8 H 9 NO 4 S, is of interest as a precursor to biologically active sulfur-containing heterocyclic cmpounds. The crystal structure displays the classical O-HÁ Á ÁO intermolecular hydrogen bonding typical for carboxylic acids forming dimers. Symmetry-related dimers are, in turn, linked through head-to-tail pairs of intermolecular N-HÁ Á ÁO interactions, giving rise to a zigzag chain along the c axis. Related literatureFor the synthesis and biological evaluation of sulfurcontaining heterocyclic compounds, see: Zia-ur-Rehman et al. Data collectionBruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS;Sheldrick, 1996) T min = 0.889, T max = 0.952 10301 measured reflections 2338 independent reflections 1644 reflections with I > 2(I) R int = 0.037

N-[Amino(azido)methylidene]-4-methylbenzenesulfonamide

“…For the synthesis, see: Arshad et al (2009). For the biological activity of sulfonamides, see: Moree et al (1991); Arshad et al (2008); Gennarti et al (1994). For related structures, see: Denny et al (1980); Mü ller & Bä rnighausen (1970).…”

“…Bruker APEXII CCD diffractometer 8664 measured reflections 2549 independent reflections 2343 reflections with I > 2(I) R int = 0.020 Refinement R[F 2 > 2(F 2 )] = 0.031 wR(F 2 ) = 0.088 S = 1.09 2549 reflections 152 parameters H atoms treated by a mixture of independent and constrained refinement Á max = 0.30 e Å À3 Á min = À0.29 e Å À3 Table 1 Hydrogen-bond geometry (Å , ). Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999 (Moree et al, 1991), they exhibit a broad spectrum of biological activites which include antibacterial, diuretic, hypoglycermic, anti-convulsant, HIV protease inhibitors and for the treatment of inflammatory rheumatic and non-rheumatic processes including onsets and traumatologic lesions (Arshad et al, 2008;Gennarti et al, 1994). Herein, we report the crystal structure of the title compound.…”

2-(2-Iodobenzenesulfonamido)acetic acid

“…For background on sulfonamides, or sulfa drugs, see: Pandya et al (2003). For the structure of the non-halogenated analogue, see: Arshad et al (2008b). For the synthesis of the title compound, see: Deng & Mani (2006).…”

“…1. We have previously reported on the crystal structures of the non-halogenated analogue of the title compound, 2-(phenylsulfonamido)acetic acid, (Arshad et al, 2008b), and the K + and Na + salts of 2-iodobenzenesulfonates (Arshad et al, 2008a,c). The bond lengths and angles in the title compound are similar to those reported there and are within normal ranges (Allen et al, 1987).…”

4-(4-Bromobenzenesulfonamido)benzoic acid

“…For details of the biological activity and pharmaceutical applications of sulfonamide derivatives, see: Pandya et al (2003); Supuran & Scozzafava (2000); Arshad, Khan & Zia-ur-Rehman (2008). For thiazine-related heterocycles, see: Arshad, Tahir et al (2008).…”