2,5-Dimethylanilinium nitrate

In the title salt, C8H12N+·NO3 −, all non-H atoms of the cation lie on mirror planes. The nitrate counteranion has m symmetry and acts as a hydrogen-bond acceptor of N—H⋯O hydrogen bonds, connecting the cations and anions into layers running parallel to the ab plane.

In the title salt, C 8 H 12 N + ÁNO 3 À , all non-H atoms of the cation lie on mirror planes. The nitrate counteranion has m symmetry and acts as a hydrogen-bond acceptor of N-HÁ Á ÁO hydrogen bonds, connecting the cations and anions into layers running parallel to the ab plane.

Related literature
Inorganic-organic hybrid materials display a great variety of structural topologies, see: Xiao et al. (2005). For comparative geometrical data in structures containing the same organic groups, see:  ;Souissi et al. (2009 Table 1 Hydrogen-bond geometry (Å , ).

Comment
The combination of organic molecules and inorganic materials was the starting point for the developpement of new hybrid compounds with appropriate physical and chemical properties. These materials have a great interest due to their enormous variety of intriguing structural topologies (Xiao et al., 2005). In order to enrich the varieties in such kinds of hybrid materials and to investigate the influence of hydrogen bonds on the structural features, we report the crystal structure of 2,5 dimethylanilinium nitrate (I).
The title compound crystallizes in the space group Pcmn. Only the non-hydrogen atoms of the cation lie on the mirror planes. As shown in Fig. 1, the asymmetric unit of the crystal structure of this salt is built of half nitrate anion and half 2,5-dimethylanilinium cation. A projection of the structure along the a axis shows that the nitrate anions establish with the ammonium cations multiple hydrogen bonds, to form two inorganic layers at z = 1/4 and 3/4.
The examination of the organic cation shows that the values of the N-C, C-C distances and N-C-C, C-C-C angles range from 1.379 (4) to 1.516 (5) Å and 116. 2(3) to 122.4 (3)°, respectively. These values are similar to those obtained in other organic materials containing the same organic groups Souissi et al. 2009).

Experimental
An ethanolic solution of 2,5-dimethylaniline (10 mmol, in 5 ml) was added drop wise to a magnetically stirred aqueous solution of nitric acid HNO 3 (1 M, 10 ml) in equimolar ratio. The so-obtained solution is then filtered to eliminate the white precipitated formed and then stirred for 1 h. After stirring, the reaction mixture was kept at room temperature until apparition of transparent single crystals of 2,5-dimethylanilinium nitrate.

Refinement
The nitrogen H atoms were located in a difference map and freely refined. The other H atoms were positioned geometrically(C-H = 0.93-0.96 Å) and refined as riding with U iso (H) = 1.2Ueq (C) or 1.5 U eq (methyl C).