1-[2-(Dimethylazaniumyl)ethyl]-1H-1,2,3,4-tetrazole-5-thiolate

In the crystal structure of the title zwitterion, C5H11N5S, molecules are linked via N—H⋯N hydrogen bonds, forming zigzag chains propagating along [010]. The chains are linked by C—H⋯S hydrogen bonds, forming two dimensional networks lying parallel to (001).

In the crystal structure of the title zwitterion, C 5 H 11 N 5 S, molecules are linked via N-HÁ Á ÁN hydrogen bonds, forming zigzag chains propagating along [010]. The chains are linked by C-HÁ Á ÁS hydrogen bonds, forming two dimensional networks lying parallel to (001).
crystallizes with one molecule in the asymmetric unit and it exists as a zwitterion with the positive charge on the ammonium nitrogen atom and the negative charge on the thiolate sulfur atom (Fig 1).
This compound exists as a zwitterion like many other amino compounds reported in the literature (Ruanwas, et al., 2012;Ha, 2012). There is an intramolecular exchange of thiol proton to amino nitrogen and thus thiolate formation, which leads to the generation of a nucleophilic sulfur species (responsible for the inhibition activity). The geometry of the tert-ammonium group is found to be tetrahedral with bond angles ranging from 106.9 (11)-113.32 (9)°. The maximum deviation of the side chain at N1 position from the mean plane of tetrazole ring moiety is found to be 0.313 (10) Å. The molecular confirmation is inferred from the torsion angles N1-C2-C3-N5, C2-C3-N5-C4 and C2-C3-N5-C5 and the values are found to be -81.52 (12)°, -166.23 (9)°, and 70.26 (12)° respectively.
Two inversion related zwitterions present in the same plane are linked by a strong N-H···N hydrogen bond involving tert-ammonium group and ring N4 i atom [symmetry code: -x + 2, y -1/2, -z + 1/2] (Table 1). This interaction extends along b axis leading to the generation of a wave like supramolecular chain. The supramolecular chains in the adjacent planes are connected via a weak C-H···S hydrogen bond. This hydrogen bond links one of the methyl C-H groups and S1 ii atom [symmetry code: x -1, y, z] and generates another wave like supramolecular chain extending along a axis. The centrosymmetric N-H···N linkage between two zwitterions facilitates the effective occurrence of C-H···S hydrogen bond thus forming a ring motif with a graph set of R 4 4 (23). This motif exists in both a and b axis and generates a two dimensional network as shown in Fig. 2

Experimental
The title compound was obtained by dissolving DMETT (Sigma-Aldrich; 43.3mg, 0.25 mmol) in 20 ml of hot methanol, warming the resultant solution over a water bath for half an hour and then keeping it at room temperature for crystallization. After a week's time, colorless prismatic crystals were obtained

Refinement
The hydrogen atoms for the ammonium group (NH 4 + ) was located in a difference Fourier map and refined freely. All other hydrogen atoms were positioned geometrically (C-H = 0.98-0.99 A) and were refined using a riding model, with U iso (H) = 1.2Ueq(C) for CH 2 or 1.5Ueq(C) for CH 3 .  The asymmetric unit of (I), shown in 50% probability displacement ellipsoids.    Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.