Bis(pyridin-2-ylmethyl)ammonium nitrate

In the title compound, C12H14N3 +·NO3 −, the mononitrate of protonated bis(pyridin-2-ylmethyl)amine, the least-squares planes defined by the non-H atoms of the two aromatic moieties intersect at an angle of 7.91 (6)°. In the crystal, N—H⋯N, N—H⋯O and C—H⋯N hydrogen bonds, as well as C—H⋯O contacts, connect the entities into a three-dimensional network. The shortest centroid–centroid distance between two aromatic systems is 3.7255 (8) Å and is apparent between the two different aromatic moieties.

The twofold-protonated amine-type nitrogen atom is present in a tetrahedral coordination environment. The angles set up by the atoms connected to it cover a range of 107.7 (11)-111.81 (9) °. The least-squares planes defined by the respective non-hydrogen atoms of the two aromatic moieties enclose an angle of 7.91 (6) ° ( Fig. 1).
In the crystal, classical hydrogen bonds of the N-H···O type are observed next to C-H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating. In addition, a C-H···N contact involving the nitrate anion is apparent. One of the N-H···O hydrogen bonds shows bifurcation. All the aforementioned contacts are exclusively established between atoms on the cation as well as the anion. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. In total, the entities of the crystal structure are connected to a three-dimensional network. In terms of graph-set analysis (Etter et al., 1990;Bernstein et al., 1995), the descriptor for the C-H···O contacts is DDDD on the unary level while the classical hydrogen bonds necessitate a DDD descriptor on the same level if the bifurcated hydrogen bond is counted as two separate hydrogen bonds. The shortest intercentroid distance between two aromatic systems is measured at 3.7255 (8) Å and is apparent between the two different aromatic moieties (Fig. 2).
The packing of the title compound in the crystal structure is shown in Figure 3.

Experimental
Lanthanum nitrate was reacted with bis(pyridin-2-ylmethyl)amine in water. Upon free evaporation of the solvent, a crystalline solid was obtained from which irregular-shaped white crystals could be selected.

Refinement
Carbon-bound H atoms were placed in calculated positions (C-H 0.95 Å for aromatic carbon atoms and C-H 0.99 Å for methylene groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U eq (C).
Both nitrogen-bound H atoms were located on a difference Fourier map and refined freely.