N,N′-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4-methylbenzenesulfonamide)

The asymmetric unit of the title compound, C20H28N2O6S2, contains one half-molecule, related to the other half by a twofold rotation axis. The two aromatic rings of the molecule make a dihedral angle of 50.91 (7)°. The O—CH2—CH2—O and N—CH2—CH2—O fragments both adopt gauche conformations, with torsion angles of 76.0 (4) and 70.4 (3)°, respectively. In the crystal, adjacent molecules are linked through N—H⋯O hydrogen bonds into chains along the a-axis direction. The chains are further connected via C—H⋯O interactions into a two-dimensional supramolecular network in the ac plane.

The asymmetric unit of the title compound, C 20 H 28 N 2 O 6 S 2 , contains one half-molecule, related to the other half by a twofold rotation axis. The two aromatic rings of the molecule make a dihedral angle of 50.91 (7) . The O-CH 2 -CH 2 -O and N-CH 2 -CH 2 -O fragments both adopt gauche conformations, with torsion angles of 76.0 (4) and 70.4 (3) , respectively. In the crystal, adjacent molecules are linked through N-HÁ Á ÁO hydrogen bonds into chains along the aaxis direction. The chains are further connected via C-HÁ Á ÁO interactions into a two-dimensional supramolecular network in the ac plane.

Experimental
A solution of p-toluenesulfonyl chloride (2.83 g, 1.48 mmol) in dry dichloromethane (25 ml) was added drop wise to a dichloromethane solution (25 ml) of 1,8-diamino-3,6-dioxaoctane (1 g, 0.675 mmol) and triethylamine (2.34 ml, 1.69 mmol) at 273 K. The mixture was stirred at room temperature overnight, washed with water and saturated solution of NaHCO 3 (3 x 10 ml) and dried over MgSO 4 . The organic layer was evaporated and the residue was dissolved in methanol.
The colorless crystals of the title compound were obtained through slow evaporation of the methanolic solution at room temperature (m.p. = 361-363 K).

Refinement
C-bound hydrogen atoms were located at the calculated positions and refined in riding mode with C-H distances of 0.93 (aryl), 0.96 (methyl) and 0.97 (methylene) Å. The amino hydrogen atom was found in a difference Fourier map and refined with a distance restraint of N-H 0.86 (2) Å. For H atoms, U iso (H) were set to 1.2 (1.5 for methyl) U eq (carrier atoms).

Figure 2
The 2-D array in the ac plane formed by N-H···O and C-H···O hydrogen bonds, depicted as dashed lines.

N,N′-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4-methylbenzenesulfonamide)
Crystal data 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.