N-(2-Nitrophenylsulfonyl)-N-(4-nitrophenylsulfonyl)methylamine

In the crystal structure of the title compound, C13H11N3O8S2, molecules are linked by intermolecular C—H⋯O hydrogen bonds into zigzag chains running parallel to the c axis. Centrosymmetrically related chains are further stabilized by aromatic π–π stacking interactions [centroid–centroid distance = 3.749 (3) Å] involving adjacent 4-nitrobenzene rings. Intramolecular C—H⋯O hydrogen bonds are also present.


Related literature
For the crystal structures of related compounds, see: Henschel et al. (1996); Curtis & Pavkovic (1983). For details of the biological activities of sulfonamide compounds, see: Kamoshita et al. (1987). For details of the application of sulfonimade catalysts, see: Zhang et al. (2007). For bondlength data, see: Allen et al. (1987).

S1. Comment
Molecules containing the sulfonimide group have been recently of interest for their applications as herbicides (Kamoshita et al., 1987) and catalysts (Zhang et al., 2007). In the present paper, the crystal structure of a new compound containing two sulfonimide groups is reported.
In the molecule of the title compound ( Fig. 1) all bond lengths are normal (Allen et al., 1987) and in a good agreement with those reported previously for similar compounds (Henschel et al., 1996;Curtis & Pavkovic, 1983). The molecular conformation is stabilized by intramolecular C-H···O hydrogen bonds (Table 1). In the crystal structure, molecules are linked by intermolecular C-H···O hydrogen bonding interactions ( Fig. 2) forming zigzag chains running parallel to the c axis. Centrosymmetrically related chains are further stabilized by aromatic π-π stacking interactions occurring between adjacent the 4-nitrobenzene rings with a centroid-centroid distance of 3.749 (3) Å.

S2. Experimental
A solution of 4-nitro-benzene-1-sulfonyl chloride (10 mmol, 2.21 g) in anhydrous CH 2 Cl 2 (10 mL) was dropwise added over a period of 10 min to a solution of 2-nitro-N-methyl-benzenesulfonamide (10 mmol, 2.16 g) and EtN(i-Pr) 2 (3 mmol) in CH 2 Cl 2 (10 mL) at 273K. The mixture was stirred at room temperature for 4 h. The organic phase was washed with 2N HCl twice and dried over anhydrous Na 2 SO 4 . The solvent was removed and the residue was purified by flash chromatography (2:1 cyclohexane/dichloromethane) to give the title compound as a white solid (2.81 mg, 70% yield).
Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethanol/dichloromethane solution (1:1 v/v) at room temperature.

S3. Refinement
H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 or 0.98 Å and with U iso (H) = 1.2 (1.5 for methyl groups) times U eq (C). supporting information sup-2 . E64, o1885

Figure 1
The molecular structure of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.