N,N′-Bis(4-methylphenylsulfonyl)suberamide

In the crystal structure of the title compound, C22H28N2O6S2, the asymmetric unit contains one half molecule with a center of symmetry at the mid-point of the central C—C bond. The conformations of all the N—H, C= O and C—H bonds in the central amide and aliphatic segments are anti to their adjacent bonds. The molecule is bent at the S atom with an C—SO2—NH—C(O) torsion angle of −76.4 (3)°. The dihedral angle between the benzene ring and the SO2—NH—C(O) segment in the two halves of the molecule is 67.2 (1)°. In the crystal, N—H⋯O(C) intermolecular hydrogen bonds link the molecules into chains along the b axis.

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2239).
The dihedral angle between the benzene ring and the SO 2 -NH-C(O) segment in the two halves of the molecule is 67.2 (1)°, compared to the value of 79.5 (2)° in (II).
The structure shows simultaneous of N-H···O(C) and N-H···O(S) intermolecular hydrogen bonds (Table 1), which link the molecules into infinite chains along the b-axis.
Experimental N,N-Bis(4-methylphenylsulfonyl)-suberamide was prepared by refluxing a mixture of suberic acid (0.01 mol) with 4-methylbenzenesulfonamide (0.02 mol) and POCl 3 (0.02 mol) for 1 h on a water bath. The reaction mixture was allowed to cool and added ether to it. The solid product obtained was filtered, washed thoroughly with ether and hot ethanol. The compound was recrystallized to the constant melting point and was characterized by its infrared and NMR spectra.
Plate like colorless single crystals used in the X-ray diffraction studies were grown by a slow evaporation of a solution of the compound in ethanol at room temperature.

Refinement
The H atom of the NH group was located in a difference map and later restrained to the distance N-H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with the aromatic C-H = 0.93 Å, the methyl supplementary materials sup-2 C-H = 0.96Å and the methylene C-H = 0.97 Å. All H atoms were refined with isotropic displacement parameters. The U iso (H) values were set at 1.2U eq (C-aromatic, N) and 1.5U eq (C-methyl). Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radii (Symmetry code: (i) -x + 2, -y + 2, -z + 1).  as those based on F, and R-factors based on ALL data will be even larger.