2,2-Dibenzylhydrazin-1-ium chloride

In the title salt, C14H17N2 +·Cl−, the central N atom is pyramidal (sum of bond angles = 330.9°) and there is a near orthogonal relationship between the benzene rings [dihedral angle = 89.95 (10)°]. The crystal packing features N—H⋯Cl hydrogen bonds, which lead to a supramolecular undulating ribbon along the a axis comprising edge-shared eight-membered {⋯HNH⋯Cl}2 synthons. The chains are connected into layers in the ab plane by C—H⋯π interactions.

In the title salt, C 14 H 17 N 2 + ÁCl À , the central N atom is pyramidal (sum of bond angles = 330.9 ) and there is a near orthogonal relationship between the benzene rings [dihedral angle = 89.95 (10) ]. The crystal packing features N-HÁ Á ÁCl hydrogen bonds, which lead to a supramolecular undulating ribbon along the a axis comprising edge-shared eightmembered {Á Á ÁHNHÁ Á ÁCl} 2 synthons. The chains are connected into layers in the ab plane by C-HÁ Á Á interactions.

Related literature
For background to the synthesis of S-substituted dithiocarbazates and their metal complexes, see: Ravoof et al. (2010); Tayamon et al. (2012). For the synthesis, see : Tarafder et al. (2000). For the structure of the diphenyl analogue of the cation, see: Stender et al. (2003).

Crouse and Edward R. T. Tiekink Comment
In continuation of efforts to explore the structure-activity relationships of new S-substituted dithiocarbazates and their metal complexes (Ravoof et al., 2010;Tayamon et al., 2012), the title salt (I) was obtained during an attempt to prepare the benzylhydrazine analogue of S-benzyldithiocarbazate.
The asymmetric unit of salt (I) comprises a 2,2-dibenzylhydrazinium cation and a chloride anion, Fig. 1. The sum of the angles about the N1 atom approximates 331° confirming its pyramidal nature. The dihedral angle between the phenyl rings is 89.95 (10)°, thereby displaying an orthogonal relationship. Hydrazinium cations are comparatively rare in the crystallographic literature with the most closely related structure being that of the diphenyl analogue, isolated as its (Stender et al., 2003). The N-N distance in this structure of 1.453 (5) Å is indistinguishable from that in (I) of 1.453 (2) Å.
The crystal packing is dominated by N-H···Cl hydrogen bonds, Table 1. Each ammonium-H atom forms a hydrogen atom with a chloride to generate an undulating ribbon along the a axis comprising edge-shared eight-membered {···HNH···Cl} 2 synthons, Fig. 2. These are connected into layers in the ab plane by C-H···π interactions, Fig. 3 and Table   2. Layers stack along the c axis with no specific interactions between them.

Experimental
The title compound was isolated as a side-product during the synthesis of a benzylhydrazine analogue of S-benzyldithiocarbazate using a procedure adapted from Tarafder et al. (2000). Potassium hydroxide (0.02 mol, 1.12 g) and benzylhydrazine (0.02 mol, 3.9 g) were each completely dissolved in chloroform (20 ml). The benzylhydrazine solution was added to the cooled mixture of potassium hydroxide. The combined solution was kept in an ice-salt bath while carbon disulfide (0.02 mol, 1.52 g) was added with constant stirring over one hour. Benzylchloride (0.02 mol, 2.3 ml) was added drop-wise to the above mixture with vigorous stirring. The initial precipitate was removed by filtration and then diethyl ether was added to the solution. A precipitate (0.63 g) was filtered from the solution after one day. Pale-yellow crystals of the title salt (M.pt > 583 K) were harvested from the filtrate on the second day (0.30 g).

Refinement
Carbon-bound H-atoms were placed in calculated positions (C-H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U iso (H) = 1.2U equiv (C). The nitrogen-bound H-atoms were refined freely.   Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figure 1
The molecular structure of salt (I) showing displacement ellipsoids at the 50% probability level.

2,2-Dibenzylhydrazin-1-ium chloride
Crystal data C 14 H 17 N 2 + ·Cl − M r = 248.75 Triclinic, P1 Hall symbol: -P 1 a = 5.6155 (4) Å b = 9.9804 (7) Å c = 11.7302 (9) Å α = 79.532 (6) Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

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