N-Methyl-N-nitroso-p-toluenesulfonamide

The crystal structure of the title compound, C8H10N2O3S, displays predominant C—H⋯O hydrogen-bonding and π–π stacking interactions. The hydrogen bonds are between the O atoms of the sulfonyl group and H atoms on methyl groups. The π–π stacking interactions occur between adjacent aromatic rings, with a centroid–centroid distance of 3.868 (11) Å. These interactions lead to the formation of chains parallel to (101).

The crystal structure of the title compound, C 8 H 10 N 2 O 3 S, displays predominant C-HÁ Á ÁO hydrogen-bonding andstacking interactions. The hydrogen bonds are between the O atoms of the sulfonyl group and H atoms on methyl groups. Thestacking interactions occur between adjacent aromatic rings, with a centroid-centroid distance of 3.868 (11) Å . These interactions lead to the formation of chains parallel to (101).

Related literature
For the use of the title compound as a nitrosylating agent, see: Mayer et al. (2014). For related structures, see: Hakkinen et al. (1988); Lightfoot et al. (1993). For the use of the title compound as a potential cancer chemotherapeutic, see: Garcia-Rio et al. (2011);Skinner et al. (1960). For its use as an antimicrobial, see: Uri & Scola (1992) and as a precursor in methylene production and production of heterocyclic rings, see: Hudlicky (1980). For literature hydrogen-bond lengths between sulfonyl O atoms and methyl H atoms in sulfonamide structures, see: Dodoff et al. (2004). For the potential use of sulfonamide compounds as ligands for metal coordination, see: Jacobs et al. (2013).  Table 1 Hydrogen-bond geometry (Å , ). (2) 3.401 (2) 160

Comment
Diazald (N-methyl-N-nitroso-p-toluenesulfonamide) has been known to be a versatile reagent used in the general synthesis of diazomethane, a useful compound that serves as a precursor for methylene production and is used in the production of heterocyclic rings. (Hudlicky, 1980) Recently, these N-nitroso compounds have gained attention due to their potential cancer chemotherapeutic abilities. (Skinner et al., 1960); (Garcia-Rio et al., 2011) Additionally, the title compound was also found to behave as an antimicrobial agent against yeasts, fungi, Gram-negative, and Gram-positive bacteria. (Uri & Scola, 1992) The title compound was also shown to behave as a nitrosylating reagent in the formation of a new diruthenium complex. (Mayer et al., 2014) Specifically, our group has investigated the potential of these sulfonamide structures as ligands for metal coordination. (Jacobs et al., 2013) Here we report on the crystal structure of this versatile compound. This compound forms hydrogen bonds of 2.49 (2) Å between the oxygen atom (O1) on the sulfonyl group of one molecule and the hydrogen atom (H10B) on the methyl group of another. These hydrogen bond lengths were confirmed to be in the normal range (2.31 (6) Å -2.53 (12) Å) between sulfonyl O atoms and methyl H atoms on sulfonamide structures. (Dodoff et al., 2004) Additionally, pi-stacking interactions exist between adjacent aromatic rings and measure 3.868 (11) Å. These pi-stacking and hydrogen bonding interactions produce a stabilized dimerized crystal structure resulting in parallel chains.

Experimental
Approximately 100 mg of the title compound were dissolved in 2 ml of 100% isopropyl alcohol solution after being heated to boiling conditions. The solution was allowed to evaporate slowly for three days at approximately 4 C until clear, colorless crystals were formed. A crystal was manually separated and analyzed for crystallographic data using a Bruker APEXII CCD single-crystal X-ray diffractometer.

Refinement
The structure was solved using direct methods (Bruker, 2011). Hydrogen 8 A, 8B, 8 C were found by electron difference maps and then allowed to vary in 3 dimensions. The isotropic parameter was held to -1.2.  Thermal ellipsoid plot at 50% probability.

Figure 2
The title structure is stabilized by a hydrogen bond between O2 and H8C, which measures 2.49 (2) Å and pi-stacking interactions between adjacent benzene rings, which measures 3.871 (11) Å. Oxygen atoms are shown in red, carbon atoms in black, hydrogen atoms in white, and nitrogen atoms in blue. Symmetry equivalent pi-stacking and hydrogen bonding are indicated by red and blue dashed lines, respectively. 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.