N-(4-Methoxybenzoyl)-2-methylbenzenesulfonamide

In the title compound, C15H15NO4S, the dihedral angle between the aromatic rings is 80.81 (1)° and the dihedral angle between the planes defined by the S—N—C=O fragment and the sulfonyl benzene ring is 86.34 (1)°. In the extended structure, dimers related by a crystallographic twofold axis are connected by pairs of both N—H⋯O hydrogen bonds and C—H⋯O interactions, which generate R 2 2(8) and R 2 2(14) loops, respectively. A weak aromatic π–π stacking interaction is also observed [centroid–centroid separation = 3.7305 (3) Å].

In the title compound, C 15 H 15 NO 4 S, the dihedral angle between the aromatic rings is 80.81 (1) and the dihedral angle between the planes defined by the S-N-C=O fragment and the sulfonyl benzene ring is 86.34 (1) . In the extended structure, dimers related by a crystallographic twofold axis are connected by pairs of both N-HÁ Á ÁO hydrogen bonds and C-HÁ Á ÁO interactions, which generate R 2 2 (8) and R 2 2 (14) loops, respectively. A weak aromaticstacking interaction is also observed [centroid-centroid separation = 3.7305 (3) Å ].

Introduction
As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Sreenivasa et al., 2014), we report here the crystal structure of the title compound (I) (Fig 1).

Synthesis and crystallization
The title compound (I) was prepared by refluxing a mixture of 4-methoxybenzoic acid, 2-methylbenzenesulfonamide and phosphorous oxychloride (POCl 3 ) for 2 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid obtained was filtered and 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 compound obtained was filtered and later dried (Melting point: 447 K).
Colorless prisms of (I) were obtained from a slow evaporation of its aqueous methanolic solution at room temperature.

Refinement
The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C-H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the U eq of the parent atom).
Further, the molecule is twisted at the S atom, the dihedral angle between the planes defined by the S-N-C=O segment in the central chain and the sulfonyl benzene ring being 86.34 (1)°.
The supramolecular architecture of I is built in three stages. In the first stage, the molecules are linked into dimers by a crystallographic twofold axis through strong N1-H1···O2 hydrogen bonds, thus generating R 2 2 (8)  motif. In the third stage, π(methylphenyl) ···π(methylphenyl) interactions stabilize the structure, Cg(methylphenyl) ···Cg(methylphenyl) distance being 3.7305 (3)Å (Figure 3). The geometries and symmetry operations of various interactions are shown in Table 1.

Figure 1
Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Special details
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. 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 > 2σ(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.