2,6-Di(pyrrolidin-1-yl)pyridinium chloride monohydrate

In the organic cation of the title compound, C13H20N3 +·Cl−·H2O, the two pyrrolidine rings adopt twisted conformations. The pyridine ring makes dihedral angles of 14.57 (6) and 23.96 (6)° with the mean planes of the pyrrolidine rings. In the crystal structure, pairs of bifurcated intermolecular O—H⋯Cl hydrogen bonds link the water molecules and chloride anions into an R 4 4(8) ring motif. Intermolecular N—H⋯Cl, C—H⋯Cl and C—H⋯O hydrogen bonds further interconnect these rings with the organic cations into a two-dimensional network parallel to the bc plane.

In the organic cation of the title compound, C 13 H 20 N 3 + Á-Cl À ÁH 2 O, the two pyrrolidine rings adopt twisted conformations. The pyridine ring makes dihedral angles of 14.57 (6) and 23.96 (6) with the mean planes of the pyrrolidine rings. In the crystal structure, pairs of bifurcated intermolecular O-HÁ Á ÁCl hydrogen bonds link the water molecules and chloride anions into an R 4 4 (8) ring motif. Intermolecular N-HÁ Á ÁCl, C-HÁ Á ÁCl and C-HÁ Á ÁO hydrogen bonds further interconnect these rings with the organic cations into a twodimensional network parallel to the bc plane.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 (Zhu et al., 2003;Fetzner, 1998). The metabolic activation of the heterocyclic compounds and the DNA damage produced (Xue & Warshawsky, 2005) as well as their roles as a pollutants (Padoley et al., 2008) and their deposition on land and coastal environments (Cornell et al., 2003) have been reported. The title compound can be used for the synthesis of new organometallic complexes and in the field of biological activity and drug design.

Experimental
In a two-neck round bottom flask, pyridine (0.01 mol, 1.0 g) was dissolved in THF (50 ml). The flask was connected to dropping funnel containing anhydrous aluminum chloride (2.7 g, 0.02 mol) dissolved in THF (25 ml) and ended with anhydrous calcium chloride drying tube. In an ice bath, the aluminum chloride solution was added in small portions and the temperature was maintained between 273-278 K during the addition. The mixture was refluxed for 30 mins at 323-328 K under dry condition. Pyrrolidine (0.02 mol, 1.5 g) was added in small portions to the formed red colour reaction mixture.
After stirring for 1 h, the mixture was decanted on ice water and the organic layer was extracted with butanol. The solvent was evaporated by using the rotary evaporator. Deep brown single crystals were formed after one week at room temperature and washed with methanol and dried at room temperature. constrained to ride with their parent atoms, with U iso (H) = 1.2U eq (N) or 1.5U eq (O). The remaining H atoms were placed in calculated positions (C-H = 0.93 or 0.97 Å), with U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of the title salt, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.