Bis(benzothiazol-2-ylmethyl)amine

In the title compound, C16H13N3S2, the dihedral angle between the two benzothiazole ring systems is 20.41 (2)°. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link molecules into a chain along the b axis. The packing is further stabilized by C—H⋯π stacking interactions involving the two benzothiazole ring systems.


Related literature
Benzothiazole devivatives have been used as photostablizers and metal chelating agents (Pinheiro et al., 1990;Emad et al., 2009). Many chelating heterocyclic ligands bearing benzothiazole group have been reported in recent years (Oughtred et al., 1982;Akther et al., 2008). The wide range of application of the benzothiazole chelators and their metal complexes aroused our interest to prepare a new series of metal complexes. With this mind, the title compound was prepared and we report the crystal stucture herein.
In the molecular structure ( Fig. 1), the dihedral angle between the two benzothiazole ring systems is 20.41 (2)°. The C -N bond distances range from 1.2906 (18) to 1.4567 (18) Å, and the C-N(amino) bonds are longer than the C-N (benzothiazolyl) bonds. In the crystal structure ( Fig. 2), intermolecular N-H···N hydrogen bond links molecules into a chain along the b axis. The packing is further stabilized by C-H···π stacking interactions involving two benzothiazole ring systems.

S2. Experimental
The title compound was synthesized according to a literature procedure (Laurence et al., 1980). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution at room temperature.

S3. Refinement
H atoms bonded to carbon atoms were placed in idealized positions [C-H(methylene)=0.97 Å and C-H(aromatic) =0.93 Å] and included in therefinement in the riding-model approximation, with U iso (methyl and aromatic H) = 1.2Ueq(C). H atoms bonded to N atom was found from the difference map and refined with the restraint of N-H=0.86 (1)Å and U iso (H)=1.2U eq (N).

Figure 1
The molecular structure with displacement ellipsoids drawn at the 50% probability level.  Part of the crystal structure showing hydrogen bonds as dashed lines.

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 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.