N-Benzylaniline

The title compound, C13H13N, is an N-alkylated derivative of aniline. The N atom is present in a nearly planar molecular geometry (angles sums at the N atom are 358 and 359° in the two molecules of the asymmetric unit). The planes defined by the aromatic rings intersect at angles of 80.76 (4) and 81.40 (4)° in the two molecules. In the crystal, N—H⋯Cg interactions connect the two molecules of the asymmetric unit to form infinite homodromic chains along the crystallographic b axis [N⋯π = 3.4782 (12) and 3.4642 (13) Å].

The title compound, C 13 H 13 N, is an N-alkylated derivative of aniline. The N atom is present in a nearly planar molecular geometry (angles sums at the N atom are 358 and 359 in the two molecules of the asymmetric unit). The planes defined by the aromatic rings intersect at angles of 80.76 (4) and 81.40 (4) in the two molecules. In the crystal, N-HÁ Á ÁCg interactions connect the two molecules of the asymmetric unit to form infinite homodromic chains along the crystallographic b axis [NÁ Á Á = 3.4782 (12) and 3.4642 (13) Å ].

Related literature
For the crystal structure analysis of a ruthenium coordination compound featuring the title compound as a ligand, see: Casey et al. (2006). For the crystal structure analysis of a rhodium coordination compound containing the title compound as a ligand, see: Marcazzan et al. (2003).  Table 1 Hydrogen-bond geometry (Å , ).

Comment
The coordination behaviour of monodentate ligands is influenced by electronic as well as steric factors. In this aspect, derivatives of aniline are particularily interesting and promising compounds due to a series of reasons: first, they can act as neutral or -upon deprotonation -as anionic ligands. Second, the derivatization of the aromatic system of aniline allows for the fine-tuning of the basicity and nucleophilicity of the N atom and thus its coordination behaviour in terms of Lewis basicity. Third, the steric pretense of the ligand can be varied by applying different patterns of substituents among the aromatic regime as well as by endowing the N atom itself with sterically more demanding groups. In our continuous efforts to elucidate the coordination behaviour of N donor ligands, it seemed necessary to determine the crystal structure of the title compound to enable comparative studies with the coordination compounds obtained. So far, only two structure determinations involving the title compound as a ligand are present in the literature (Casey et al., 2006;Marcazzan et al., 2003).
The molecular geometry around both molecules of the asymmetric unit is essentially planar with X-N-Y angles ranging from 117.0 (10)° to 124.54 (11)°. The biggest of these angles in the title compound is found for both molecules for the C-N-C angle. The phenyl rings within one molecule of the asymmetric unit are nearly orientated perpendicular to each other, the least-squares planes defined by the aromatic rings within one molecule enclose angles of 80.76 (4)° and 81.40 (4)°, respectively (Fig. 1).
The N-H groups do not interact with each other. Instead, the formation of N-H···Cg contacts is observed in the crystal structure. These contacts exclusively use the aromatic moiety of the benzyl substituent as acceptor and are present only between one of the molecules of the asymmetric unit and its translation symmetry-generated equivalents (Fig. 2). In total, the formation of two one-dimensional chains of molecules along the crystallographic b axis is observed.
The packing of the title compound is shown in Fig. 3.

Experimental
The compound was obtained commercially (Aldrich). Crystals suitable for the X-ray diffraction study were taken directly from the provided compound.

Refinement
Carbon-bound H atoms were placed in calculated positions (C-H 0.95 Å for aromatic C atoms, C-H 0.99 Å for aliphatic C atoms) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U eq (C). The nitrogen-bound H atoms were located on a difference Fourier map and refined freely.  Fig. 1. The asymmetric unit of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).