N,N′-(Ethane-1,2-diyl)dibenzenesulfonamide

In the title compound, C14H16N2O4S2, the dihedral angle between the terminal phenyl rings is 77.07 (13)°. The geometries around the S atoms are distorted tetrahedral, with O—S—O angles of 120.66 (12) and 119.44 (11)°. In the crystal, molecules are stacked in columns along the a axis via intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

In the title compound, C 14 H 16 N 2 O 4 S 2 , the dihedral angle between the terminal phenyl rings is 77.07 (13) . The geometries around the S atoms are distorted tetrahedral, with O-S-O angles of 120.66 (12) and 119.44 (11) . In the crystal, molecules are stacked in columns along the a axis via intermolecular N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds.

Comment
Sulfonamide is found in a number of synthetic as well as natural compounds. These molecules exhibit antibacterial (Misra et al., 1982), insulin-releasing (Maren, 1976), anti-inflammatory (Li et al., 1995 and antitumor (Yoshino et al., 1992) activities. An X-ray study of the title compound was undertaken in order to determine its crystal and molecular structure owing to the biological importance of its analogues. The molecular structure is shown in Fig. 1.
The molecule is bent at the N atoms with C9-S2-N2-C8 and C7-N1-S1-C6 torsion angles of 58.48 (18) and 72.6 (2)°, respectively. The geometries around the sulfonamide S atoms are in a slightly distorted tetrahedral configuration, similar to that observed in other reported structures (Basak et al., 1982). The maximum and minimum values of the angles around S are 121.62 (17) and 105.92 (11)°, respectively. This deviation can be attributed to the non-bonded interactions involving the S-O bonds, resulting in a structure with less steric interference (Cotton & Stokley, 1970) and the varied steric bulk of the substituents. The dihedral angle between the terminal phenyl C1-C6 and C9-C14 rings is 77.07 (13)°.

Experimental
In a round bottom flask, 25ml from toluene was mixed with benzenesulfonyl chloride (0.02 mol, 3.5 g) with stirring. Drops of ethylenediamine (0.01 mol, 0.5 g ) was added and the mixture was refluxed for 30 min. The yellow gum formed was dissolved in hot water and sodium bicarbonate was added. The yellow precipitate formed was dissolved in methanol at 60°C , yielding colourless crystals.

Refinement
Atoms H1N1 and H1N2 were located from a difference Fourier map and refined freely [N- The remaining H atoms were positioned geometrically (C-H = 0.93-0.97 Å) and were refined using a riding model, with U iso (H) = 1.2U eq (C). Fig. 1

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 Rfactors(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.