N,N′-[1,3-Phenylenebis(methylene)]di-p-toluenesulfonamide

In the title compound, C22H24N2O4S2, the dihedral angles between the central benzene ring and the pendant rings are 66.96 (13) and 69.37 (13)°. The torsion angles for the C—N—S—C fragments are −68.5 (3) and −72.6 (3)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds to generate infinite (001) sheets containing R 4 4(28) loops. A weak aromatic π–π stacking contact between one of the terminal benzene rings and its inversion-related partner is also observed [centroid-to-centroid separation = 3.796 (2) Å and slippage = 1.581 Å], as are two possible C—H⋯π contacts.

In the title compound, C 22 H 24 N 2 O 4 S 2 , the dihedral angles between the central benzene ring and the pendant rings are 66.96 (13) and 69.37 (13) . The torsion angles for the C-N-S-C fragments are À68.5 (3) and À72.6 (3) . In the crystal, molecules are linked by N-HÁ Á ÁO hydrogen bonds to generate infinite (001) sheets containing R 4 4 (28) loops. A weak aromaticstacking contact between one of the terminal benzene rings and its inversion-related partner is also observed [centroid-to-centroid separation = 3.796 (2) Å and slippage = 1.581 Å ], as are two possible C-HÁ Á Á contacts.
IUK thanks the Higher Education Commission of Pakistan for financial support under the project 'Strengthening the Materials Chemistry Laboratory at GCUL'. supplementary materials . E68, o950 [doi:10.1107/S1600536812007222]

Ejaz, Islam Ullah Khan, William T. A. Harrison and Rukhsana Anjum Comment
As part of our ongoing structural studies of symmetric aromatic sulfonamides (Ejaz et al., 2011), the synthesis and crystal structure of the title compound are described herein.
The crystal structure of the diphenyl analogue has been reported on recently (Ejaz et al., 2011). There the complete molecule is generated by crystallographic twofold symmetry, but its intermolecular linkages (a layered network constructed from N-H···O hydrogen bonds supplemented by C-H···π and π-π contacts) are very similar to those seen in the crystal structure of the title compound.

Experimental
Benzene-1,3-diyldimethanamine (0.132 ml, 1.0 mmol) was mixed with 25 ml distilled water in a 50 ml round-bottom flask. 4-Methyl benzene sulfonyl chloride (0.38 g, 2.0 mmol) was added while maintaining the pH of the reaction mixture at 9.0 using 3% sodium carbonate solution. The suspension was stirred for about four hours and a white product was filtered, washed, dried and recrystallized from methanol to yield colourless crystalline flakes and chips of the title compound.

Refinement
The H atoms were placed in calculated positions (N-H = 0.93 Å; C-H = 0.93-0.97 Å) and refined as riding atoms with U iso (H) = 1.2U eq (C,N) or 1.5U eq (methyl C).  The molecular structure of the title molecule, showing the atom numbering and the displacement ellipsoids drawn at the 50% probability level.

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