Tribenzylammonium chloride

Single crystals of the title salt, C21H21NH+·Cl−, were isolated as a side product from the reaction involving [(C6H5CH2)3NH]2[HPO4] and Sn(CH3)3Cl in ethanol. Both the cation and the anion are situated on a threefold rotation axis. The central N atom in the cation has a slightly distorted tetrahedral environment, with angles ranging from 107.7 to 111.16 (10)°. In the crystal, the tribenzylammonium cations and chloride anions are linked through N—H⋯Cl and C—H⋯Cl hydrogen bonds, leading to the formation of infinite chains along [001]. The crystal studied was a merohedral twin.

In the crystal, the chloride anion is linked to the tribenzylammonium cation via N-H···Cl hydrogen bonding (Table 1).
In addition and from a supramolecular point of view, the chloride anions are also in intermolecular weak interaction with three methylinic protons of the benzyl groups of neighboring cations (Table 1). The observed distances are in the range of those reported in literature for such interactions, for example in [(C 6 H 5 CH 2 Ph 3 P] + [SnPh 3 Cl 2 ] - (Traore et al., 2013). The combination of N-H···Cl and C-H···Cl hydrogen bonding interactions leads to the formation of infinite chains along [001] (Fig. 2).
The mixture was stirred for around two hours at room temperature. Colorless crystals were obtained after one week by slow solvent evaporation.

Refinement
The H atoms,on carbon and nitrogen atoms were placed at calculated positions using a riding model with C-H = 0.95 Å (aromatic), or 0.99 Å (methylene) or N-H = 1.00 Å (amine) with U iso (H) = 1.2U eq (C or N). Intensity data revealed sup-2 Acta Cryst. (2014). E70, o618-o619 twinning by merohedry. The twin law was found by using TwinRotMat implemented in PLATON (Spek, 2009). The use of the twin law (-h-k, k, -l) and a refined twin component ratio of 0.93:0.07 reduced the reliability factor R (I>2σ(I)) from 0.042 to 0.021. The three reflections (-1 2 0; 1 1 0; -1 1 1) were affected by the beam stop and were omitted from the refinement.

Figure 1
The molecular structure of the title compound with atom labeling. Displacement ellipsoids are draw at the 30% probability level.