4-Methylbenzylammonium nitrate

In the title salt, C8H12N+·NO3 −, the N atom of the 4-methylbenzylammonium cation is displaced by 1.366 (2) Å from the mean plane of the other atoms. In the crystal, the cations are connected to the anions by N—H⋯O and N—H⋯(O,O) hydrogen bonds, generating a layered network parallel to (100). A weak C—H⋯O interaction also occurs.

In the title salt, C 8 H 12 N + ÁNO 3 À , the N atom of the 4methylbenzylammonium cation is displaced by 1.366 (2) Å from the mean plane of the other atoms. In the crystal, the cations are connected to the anions by N-HÁ Á ÁO and N-HÁ Á Á(O,O) hydrogen bonds, generating a layered network parallel to (100). A weak C-HÁ Á ÁO interaction also occurs.

Comment
We report here the preparation and the crystal structure of the title compound, C 8 H 12 N·NO 3 (I).
In the nitrate anion, the distance N2-O2 is significantly shorter than the N2-O1 and N2-O3 distances because O2 is applied in only one hydrogen bond (table1) while O1 and O3 are applied in two and three hydrogen bonds, respectively.
These geometrical features have also been noticed in other crystal structures (Rahmouni, et al., 2011).
Each organic entity is bounded to three different nitrate anions through five N-H···O hydrogen bonds forming R 1 2 (4) and R 4 2 (8) motifs ( Fig. 3) (Bernstein, et al., 1995). Examination of the 4-methylbenzylammonium cation shows that the bond distances and angles show no significant difference from those obtained in other structures involving the same organic groups (Kefi, et al., 2011). The aromatic ring of the organic cation is essentially planar with an r.m.s deviation of 0.0099 Å. The inter-planar distance between nearby phenyl rings is in the vicinity of 5.925 Å, which is much longer than 3.80 Å, value required for the formation of π-π interactions (Janiak, 2000).
The crystal cohesion and stability are ensured by electrostatic and van der Waals interactions which, together with N-H···O and C-H···O hydrogen bonds, build up a two-dimensional network.

Experimental
An aqueous solution containing 1 mmol of HNO 3 in 10 ml of water, was added to 1 mmol of 4-xylylamine in 10 ml of ethanol. The obtained solution was stirred for 20 min and then left to stand at room temperature. Colorless prisms of the title compound were obtained after some days.

Refinement
All H atoms were fixed geometrically and treated as riding with C-H = 0.93 Å (aromatic) or 0.97 Å (methylene) or 0.96

4-Methylbenzylammonium nitrate
Crystal data where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.011 Δρ max = 0.31 e Å −3 Δρ min = −0.17 e Å −3 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.