2,2′,4,4′,6,6′-Hexamethyl-N-(3-phthalimidopropyl)-N,N′-(propane-1,3-diyl)dibenzenesulfonamide

In the title compound, C32H38N3O6S2, an intermediate in the synthesis of polyamine drugs, the dihedral angle between the phenyl rings of the two 2,4,6-trimethylbenzenesulfonyl groups is 27.1 (3)°. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds, thereby forming an infinite one-dimensional chain propagating along [010].

In the title compound, C 32 H 38 N 3 O 6 S 2 , an intermediate in the synthesis of polyamine drugs, the dihedral angle between the phenyl rings of the two 2,4,6-trimethylbenzenesulfonyl groups is 27.1 (3) . In the crystal structure, molecules are linked by intermolecular N-HÁ Á ÁO hydrogen bonds, thereby forming an infinite one-dimensional chain propagating along [010].

Related literature
Polyamines are essential growth factors for cells, existing mainly as polycations at physiological pH, see: Cullis et al.  Table 1 Hydrogen-bond geometry (Å , ).
In the crystal, molecules are linked through intermolecular N-H···O hydrogen bonds to construct an infinite one-dimensional chain ( Fig. 2 and Table 1).

Experimental
Propane-1,3-diamine 1.85 g (25 mmol) was dissolved in 2 M sodium hydroxide and the solution was cooled to 0 °C, a solution of 2,4,6-trimethylbenzenesulfonyl chloride 10.9 g (50 mmol) in CH 2 Cl 2 (25 ml) was added dropwise. The reaction mixture was then stirred at room temperture for 18 h. The organic phase was separated from the aqueous phase and washed with 0.5 M HCl solution and brine. The CH 2 Cl 2 layer was dried over sodium sulfate, filtered and the solvent removed in vacuo, and the residue purified by chromatography.
A mixture of N 1 ,N 3 -Bis(mesitylenesulfonyl)-1,3-propyl-diamine 1.05 g (2.33 mmol) and 60% NaH (5.35 mmol, 0.22 g) in DMF 20 ml was stirred at 0 °C for 0.5 h, then warmed to room temperature for 0.5 h. N-(3-bromopropyl)phthalimide 1.57 g (5.82 mmol) was added and the reaction mixture was stirred at 40 °C for 4 h, then EtoH (2.5 ml) and water (5 ml) were added, the solvent was removed in vacuo at 80 °C, the residue was dissolved in CHCl 3 and washed with water, the organic layer was dried over anhydrous sodium sulfate and filtered, then concentrated in vacuo, the residue was purified by chromatography. Colorless rod crystal of (I) were obtained.

Refinement
The H atoms were positioned geogmetrically (N-H = 0.86 Å, C-H = 0.93-0.97Å) and refined as riding with U iso (H)=1.2U eq (carrier) or U iso (H)=1.5U eq (methyl-C). Fig. 1. The molecular structure of (I). Displacement ellipsoids for the non-hydrogen atoms are 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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.15326 (