N-(2-Chlorobenzoyl)-2-nitrobenzenesulfonamide

Abstract

In the title compound, C13H9ClN2O5S, the dihedral angle between the two rings is 71.2 (1)°. The crystal structure features inversion dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

N-(2-Chlorophenyl)-2-nitrobenzenesulfonamide

“…The conformation of the N-H bond in the -SO 2 -NH-segment is syn to both the ortho-nitro group in the sulfonyl benzene ring and ortho-Cl atom in the anilino ring. similar to that observed in N-(2-chlorobenzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al, 2012). The molecule is twisted at the S-N bond with the torsional angle of 74.97 20 The dihedral angle between the sulfonyl and the anilino rings is 54.97 (11)°, compared to the value of 71.2 (1)° in (I).…”

“…As part of our studies of substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al, 2011;Bowes et al, 2003;Gowda et al, 2000;Saeed et al, 2010;Shahwar et al, 2012); N-aroylsulfonamides (Suchetan et al, 2012); N-chloroarylsulfonamides (Gowda et al, 2005;Shetty & Gowda, 2004) and N-bromoarylsulfonamides (Gowda & Mahadevappa, 1983;Usha & Gowda, 2006), in the present work, the crystal structure of N-(2-Chlorophenyl)-2-nitrobenzenesulfonamide has been determined ( Fig. 1).…”

“…For studies of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al (2011); Bowes et al (2003); Gowda et al (2000), Saeed et al (2010); Shahwar et al (2012), of N-aroylsulfonamides, see: Suchetan et al (2012), of N-chloroarylsulfonamides, see: Gowda et al (2005); Shetty & Gowda (2004) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006). For hydrogen-bonding patterns and motifs, see: Adsmond & Grant (2001); Allen et al (1998); Bernstein et al (1995); Etter (1990).…”

N-(3-Chlorobenzoyl)-2-nitrobenzenesulfonamide

“…The conformation between the N-H and C═O bonds in the C-SO 2 -NH-C(O) segment is anti and the N-C bond in the segment has gauche torsion with respect to the S═O bonds ( Fig. 1), similar to that observed in N-(2-chlorobenzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al, 2012). In the title compound, the conformation between the N-H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, similar to that observed in (I).…”

“…As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al, 1999(Gowda et al, , 2006, N-(aryl)-methanesulfonamides (Gowda et al, 2007), N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al, 2012), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(3-chlorobenzoyl)-2-nitrobenzenesulfonamide has been determined ( Fig.1).…”