2-[(N-Benzyl-4-methylbenzenesulfonamido)methyl]pyridinium nitrate

In the title compound, C20H21N2O2S+·NO3 −, the dihedral angle between the pyridinium and phenyl rings is 81.77 (19)°, that between the pyridinium and tolyl rings is 1.36 (18)°, and that between the phenyl and tolyl rings is 82.69 (19)°. In the crystal, the components are linked by strong charge-assisted bifurcated N+—H⋯(O,O) hydrogen bonds and the packing is consolidated by numerous weak C—H⋯O bonds and π–π stacking interactions [for the latter, centroid–centroid separation = 3.868 (2) Å].

In the title compound, C 20 H 21 N 2 O 2 S + ÁNO 3 À , the dihedral angle between the pyridinium and phenyl rings is 81.77 (19) , that between the pyridinium and tolyl rings is 1. 36 (18) , and that between the phenyl and tolyl rings is 82.69 (19) . In the crystal, the components are linked by strong charge-assisted bifurcated N + -HÁ Á Á(O,O) hydrogen bonds and the packing is consolidated by numerous weak C-HÁ Á ÁO bonds andstacking interactions [for the latter, centroid-centroid separation = 3.868 (2) Å ].

Related literature
For the preparation of the title compound and for a related structure, see: Zhang et al. (2007).

Comment
The molecular structure of (I) (Fig. 1) shows that the nitrate is connected with its corresponding pyridinium via two strong charge-assisted N + -H···O hydrogen bonds. In the cation, the dihedral angle between the pyridinium and phenyl rings is 81.774 (9)°, that between the pyridinium and tolyl rings 1.355 (5)°, and that between the phenyl and tolyl rings 82.693 (7)°.
In the crystal structure, a series of intermolecular C-H···O interactions link the molecules (Table 1)

Experimental
The tosylamino-containing pyridine derivative was prepared by a similar method to that of Zhang et al. (2007). Colourless needles of (I) were obtained by natural evaporation from its aqueous nitric acid solution.

Refinement
The N-bound H atom was located in a difference map and refined with the distance restraint N-H = 0.91 (4) Å. The other H atoms were positioned geometrically and constrained to ride on their parent atoms [C-H distances are 0.95 and 0.99Å for aromatic and CH 2 H atoms with U iso (H) = 1.2 U eq (C), 0.98 Å, U iso = 1.5U eq (C) for CH 3 atoms. Fig. 1. The structure of (I) showing displacement ellipsoids drawn at the 30% probability level and H atoms shown as spheres of arbitrary radius.

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 Rfactors(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.