(1-Naphthylmethyl)ammonium chloride

The reaction of 1-naphthylmethylamine and hydrochloric acid in a 1:1 molar ratio resulted in the formation of the 1:1 proton-transfer compound, C11H12N+·Cl−. In the crystal, the ions are linked by N—H⋯Cl hydrogen bonds into a sheet pattern in the ab plane such that each Cl− ion is bonded to three NH groups from the naphthylmethylammonium ion.

The reaction of 1-naphthylmethylamine and hydrochloric acid in a 1:1 molar ratio resulted in the formation of the 1:1 protontransfer compound, C 11 H 12 N + ÁCl À . In the crystal, the ions are linked by N-HÁ Á ÁCl hydrogen bonds into a sheet pattern in the ab plane such that each Cl À ion is bonded to three NH groups from the naphthylmethylammonium ion.
Data collection: X-AREA; cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999  Comment 1-naphthylmethylamine has been recognized as a suitable agent in the synthesis of proton-transfer systems (Sada et al., 2004). We report here the synthesis and characterization of the title salt, 1-naphthylmethylammonium chloride. The structure shows the presence of a 1-naphthylmethylammonium species that arises from the protonation of the amine group (Fig. 1).
Hydrogen bonds play a very important role in the structure. As it is clear from Figure 2, chloride atoms engage in three hydrogen bonds with the amine group in which the chloride is in the center of triangle from three H atoms from three different cations.

Experimental
A solution of 2.5 ml of 2M hydrochloric acid was added to a solution of 5 mmol 1-naphthalenemethylamine (0.73 ml) in 30 ml pyridine. The resulting solution was stirred at 373 K for 5 h and at ambient temperature for 24 h. A pale brown solution resulted. After drying the remaining brown solid was dissolved in pure methanol. X-ray quality crystals were obtained by slow evaporation at room temperature.

Refinement
All of the H atoms bonded to C were positioned geometrically with C-H = 0.93 and 0.97Å for aromatic ring and CH 2 hydrogen atoms respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C). NH 3 hydrogens atoms were positioned from Fourier map and freely refined. Fig. 1. The molecular staucture with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level.