2-[N-(X-Chlorophenyl)carbamoyl]benzenesulfonamide (withX= 2 and 4)

Abstract

The structures of 2-[N-(2-chlorophenyl)carbamoyl]benzenesulfonamide and 2-[N-(4-chlorophenyl)carbamoyl]benzenesulfonamide, both C(13)H(11)ClN(2)O(3)S, are stabilized by extensive intra- and intermolecular hydrogen bonds. In both structures, sulfonamide groups are hydrogen bonded via the N and O atoms and form chains of molecules. The carbamoyl groups are also hydrogen bonded, involving the O and N atoms, further strengthening the polymeric chains running along the c and a axes in the 2- and 4-chloro derivatives, respectively. Carbamoylsulfonamide derivatives are novel compounds with a great potential for medicinal applications.

2-[N-(2,3-Dimethylphenyl)carbamoyl]benzenesulfonamide and the 3,4- and 2,6-dimethylphenyl analogues

“…The molecular dimensions in all three structures are in agreement with the corresponding dimensions reported for similar structures (Clark et al, 2003;Vyas et al, 2003;Singh et al, 2004;Bocelli et al, 1995;Sutton & Cody, 1989;Furuya et al, 1989;Siddiqui, Ahmad, Khan et al, 2008;Siddiqui, Ahmad, Tariq et al, 2008), with S O, S-N, S-C, N2-C7, N2-C8 and C O distances lying in very close ranges of 1.430 (2)-1.438 (2), 1.598 (3)-1.614 (3), 1.773 (3)-1.781 (3), 1.331 (4)-1.338 (4), 1.429 (4)-1.440 (4) and 1.236 (3)-1.241 (3) Å , respectively. The C-N-C angle at N2 in (II) is significantly larger than the corresponding angles in (I), (IIIA) and (IIIB).…”

“…Various biologically important saccharin skeletons and their N-alkyl derivatives have been efficiently prepared (Xu et al, 2006) by chromium oxide-catalyzed oxidation of N-alkyl-2methylarenesulfonamides in acetonitrile as well as by the already developed methodology utilizing irradiation from tungsten and mercury lamps (Masashi et al, 1999) for a similar type of conversion. In continuation of our research on 1,2benzothiazine 1,1-dioxide and saccharin derivatives (Siddiqui, Ahmad, Khan & Siddiqui, 2007;Siddiqui, Ahmad, Khan et al, 2008;Siddiqui, Ahmad, Tariq et al, 2008), we now report the syntheses and crystal structures of the title compounds, 2-[(X-dimethylphenyl)carbamoyl]benzenesulfonamide [X = 2,3-for (I), 3,4-for (II) and 2,6-for (III)]. The three dimethylphenyl-substituted analogues are closely related to the fenamate class of nonsteroidal anti-inflammatory drugs and are expected to exhibit very potent biological activities since sulfonamide and carbamoyl functions exist in the same nucleus simultaneously.…”

“…The N1 atoms in all these structures are tetrahedral, the sum of angles around this atom being in the range 334-340 . The H atoms bonded to atom N1, and atoms O1 and O2 bonded to S1, are staggered, as observed in chlorophenyl analogues of the title compounds (Siddiqui, Ahmad, Khan et al, 2008) and the compound with CSD refcode COYVER (Foresti et al, 1985). Several structures have been reported wherein the H and O atoms of the sulfonamide unit are eclipsed, e.g.…”

2,2′-(4-Methyl-4H-1,2,4-triazole-3,5-diyl)dibenzenesulfonamide

“…For background to benzisothiazole derivatives, see: Siddiqui et al (2007); Siddiqui, Ahmad, Khan et al (2008); . For related crystal structures, see: Carlsen et al (1995).…”

“…(2012). E68, o754 In continuation to our research work on the synthesis of benzisothiazole derivatives (Siddiqui, Ahmad, Khan et al, 2008;, the title compound (I), (Fig. 1) is prepared from hydrazine and commercial source of saccharin.…”