N-(3-Nitrobenzoyl)benzenesulfonamide

In the title compound, C13H10N2O5S, the C=O bond in the —SO2—NH—CO— segment is anti to the meta-nitro group in the benzoyl ring, while the N—C bond has gauche torsions with respect to the S=O bonds. The molecule is twisted at the N atom with a dihedral angle of 79.9 (2)° between the sulfonyl benzene ring and the —SO2—NH—CO— segment. Furthermore, the dihedral angle between the benzeneline rings is 86.9 (2)°. In the structure, the molecules are linked into helical chains along the b axis via N—H⋯O hydrogen bonds.


P. A. Suchetan, Sabine Foro and B. Thimme Gowda Comment
Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000(Gowda et al., , 2007, N-(substitutedbenzoyl)-arylsulfonamides (Gowda et al., 2009), N-chloroarylsulfonamides (Jyothi & Gowda, 2004 and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(3nitrobenzoyl)benzenesulfonamide has been determined ( Further, the C=O bond in the segment is anti to the meta-nitro group in the benzoyl ring, while the conformation of the N-C bond in the C-SO 2 -NH-C(O) segment of the structure has "gauche" torsions with respect to the S═O bonds.
The molecule is twisted at the N atom with a dihedral angle of 79.9 (2)° between the sulfonyl benzene ring and the C-SO 2 -NH-C-O segment, compared to the value of 79.6 (1)° in (I).
The dihedral angles between the sulfonyl and the benzoyl benzene rings is 86.9 (2)°, compared to the value of 89.3 (1)° in (I).
The packing of molecules linked by of N-H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Experimental
The title compound was prepared by refluxing a mixture of 3-nitrobenzoic acid, benzene sulfonamide and phosphorous oxy chloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point.
Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of the solvent from its toluene solution at room temperature.

Refinement
The H atom of the NH group was located in a difference map and later restrained to N-H = 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C-H = 0.93 Å. All H atoms were refined with isotropic displacement parameters set to 1.2 times of the U eq of the parent atom. software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figure 1
Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

N-(3-Nitrobenzoyl)benzenesulfonamide
Crystal data Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.