N,N′-Bis(2-chlorophenylsulfonyl)adipamide

In the centrosymmetric title compound, C18H18Cl2N2O6S2, the conformation of the N—H and C=O bonds in the C—SO2—NH—C(O)—C—C segment is anti to each other. The dihedral angle between the planes of the benzene ring and the central part of the molecule is 89.6 (2)°. In the crystal, intermolecular N—H⋯O(S) hydrogen bonds link the molecules into sheets along the b axis.

VZR thanks the University Grants Commission, Government of India, New Delhi, for award of a research fellowship.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2284).
The dihedral angle between the planes of the benzene ring and the SO 2 -NH-C(O)-C-C segment in (I) is 89.6 (2)°, compared to the value of 89.9 (1)° in (II).
N-H···O1(S) H-bond formation results in an S=O1 bond longer than the S=O2 bond. A series of N-H···O(S) intermolecular hydrogen bonds (Table 1) link the molecules into sheets running in the direction of b axis (Fig. 2).
Experimental N,N-Bis(2-chlorophenylsulfonyl)-adipamide was prepared by refluxing a mixture of adipic acid (0.01 mol) with 2chlorobenzenesulfonamide (0.02 mol) and POCl 3 for 1 hr 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.
Needle like colorless single crystals used in the x-ray diffraction studies were grown by a slow evaporation of the solution of the compound in ethanol at room temperature.

Refinement
The H atom of the NH group was located in a difference Fourier map and later restrained to the distance N-H = 0.86 (3) Å. The other H atoms were positioned with idealized geometry using a riding model with aromatic C-H distance = 0.93 Å and methylene C-H = 0.97 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U eq of the parent atom).