N-(2-Chlorobenzoyl)-4-methylbenzenesulfonamide

In the title compound, C14H12ClNO3S, the C=O bond is syn to the Cl substituent in the adjacent benzene ring. The C—S—N—C torsion angle is −80.6 (6)°. The chlorobenzoyl ring is disordered and was refined using a split model [occupancy ratio 0.537 (3):0.463 (3)]. In the crystal, molecules are linked by pairs of N—H⋯O(S) hydrogen bonds, forming inversion dimers.

In the title compound, C 14 H 12 ClNO 3 S, the C O bond is syn to the Cl substituent in the adjacent benzene ring. The C-S-N-C torsion angle is À80.6 (6) . The chlorobenzoyl ring is disordered and was refined using a split model [occupancy ratio 0.537 (3):0.463 (3)]. In the crystal, molecules are linked by pairs of N-HÁ Á ÁO(S) hydrogen bonds, forming inversion dimers.

P. A. Suchetan, Sabine Foro and B. Thimme Gowda Comment
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., 2010), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(2-chlorobenzoyl)-4-methylbenzenesulfonamide (I) has been determined. The conformation of the N-H bond in the C-SO 2 -NH-C(O) segment is anti to the C=O bond ( Fig. 1), similar to that observed in i>N-(2-chlorobenzoyl)-4-chlorobenzenesulfonamide (II) (Gowda et al., 2010). Further, the conformation of the C=O bond in the C-SO 2 -NH-C(O) segment of (I) is syn to the ortho-Cl in the benzoyl ring, similar to that observed between in (II).
The molecules are twisted at the S atom with the torsional angle of -80.6 (6)°, compared to that of 65.7 (2)° in (II).
The dihedral angle between the sulfonyl benzene ring and the -SO 2 -NH-C-O segment is 65.0 (5)°, compared to the value of 88.5 (1)° in (II).
Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 66.1 (2)°, compared to the value of 58.2 (1)° in (II).
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 2-chlorobenzoic acid, 4-methylbenzenesulfonamide and phosphorous oxy chloride for 3 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. It was filtered, dried and recrystallized.
Prism like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of the solvent in its toluene solution at room temperature.

Refinement
The H atoms were positioned with idealized geometry using a riding model with C-H distances of 0.93 Å (C-aromatic) and 0.96 Å (C-methyl) and N-H = 0.86 (2) %A.
U iso (H) values were set at 1.2 U eq (C-aromatic, N) and 1.5 U eq (C-methyl).
The chlorobenzyol ring with atoms C8, C9, C10, C11, C12, C13 and CL1 is disordered and was refined using a split model. The corresponding site-occupation factors were refined so that their sum was unity [0.536 (4)-0.464 (4)]. The corresponding bond distances in the disordered groups were restrained to be equal. The C atoms of lower occupancy were refined isotropic.

N-(2-Chlorobenzoyl)-4-methylbenzenesulfonamide
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.