N-Benzyl-3-nitroaniline

The molecule of the title compound, C13H12N2O2, has a bent conformation with a torsion angle about the central C—N bond of 72.55 (19)°. In the crystal, the molecules are connected via classical N—H⋯O and non-classical C—H⋯O hydrogen bonds into chains along [10]. The dihedral angle between the ring planes is 86.0 (6)°.


Experimental
Crystal data

Comment
The synthesis of the title compound was a part of Preparatory problems for the 40th International Chemistry Olympiad (Magyarfalvi, 2008). It was prepared and crystalized as a part of the laboratory work with high-school students.
The N-methyl-3-nitroaniline system is almost perfectly planar (the mean plane of the the phenyl ring is at an angle of 1.5 (2)° with the mean plane of the angle nitro group, and 1.4 (2)° with the mean plane of the central C1-N1-C7. The phenyl substituent is at an angle of 86.0 (2)° to the rest of the molecule. The C1-N1-C7-C8 torsion angle is 72.55 (19)°.
This conforamtion is similar to thet reported by Betz et al. (2011) for the unsubstituited N-benzylaniline.
Interestingly, in a similar compound, N-benzyl-4-nitroaniline (Iwasaki et al., 1988), the N-H···O bonding is entirely absent, which demonstrates the effect of changing the position of the nitro group on tha supramolecular aggregation.

Experimental
The title compound was prepared using a slightly modified procedure (Magyarfalvi, 2008) and isolated in a form of yellow crystalline powder. A sample of approximately 100 mg of the compound was dissolved in approximately 10 ml of hot ethanol. The solution was left to cool to room temperature, filtered, and the filtrate was left to crystallize by slow evaporation.
The single crystalls suitable for X-ray study were obtained after aproximatelly 4 days.

Refinement
The amine hydrogen atom was locates from the electron fifference map and isotropical refined. All H atoms bonded to carbon atoms were placed geometrically and included in the refinement in the riding-model approximation with C-H distances of 0.93Å for aryl and 0.97Å for CH 2 . In the refinement these H atoms were included with U iso = 1.2U eq (C).
Since there are no heavy atoms in the structure, the Friedel pairs (1186) were merged for the final refinement.
supplementary materials sup-2 Figures Fig. 1. The molecular structure of title compound with the atom labeling scheme. Displacement ellipsoids are shown at 30% probability level. Hydrogen atoms are shown as a spheres of arbitrary radius.