1-(3-Phenylprop-2-ynyl)pyrrolidinium chloride

The title compound C13H16N+·Cl−, an achiral salt, was synthesized by a three-component coupling reaction in the presence of copper(I) iodide. The configuration of five-membered ring is close to an envelope conformation. The crystal structure is stabilized by intermolecular C—H⋯Cl and N—H⋯Cl interactions.

The title compound C 13 H 16 N + ÁCl À , an achiral salt, was synthesized by a three-component coupling reaction in the presence of copper(I) iodide. The configuration of fivemembered ring is close to an envelope conformation. The crystal structure is stabilized by intermolecular C-HÁ Á ÁCl and N-HÁ Á ÁCl interactions.
The author is grateful to Central China Normal University for support.  (Konishi et al., 1990;Hattori et al., 1993;Dyker et al.,1999). The reaction which a three component procedure between terminal alkynes, formaldehyde and secondary amines and give rise to the propargylamines with rapid reaction rates by the introduction of copper (I) catalysts.
Here we report the crystal structure of the title compound (Fig. 1). The length of the N1-C9 bond in this compound was found to be 1.479 Å, which is approximate with the length of ordinary N-C single bond (1.47 Å).The four carbon atoms of the five-member ring are not in the same plane, the torsion angle is 14.92 °. It was close to the envelope conformation.
X-ray analysis reveals that the crystal structure is stabilized by C-H···Cl interaction and N-H···Cl interaction.

Experimental
The title compound was synthesized according to the literature procedure of Nilsson et al. (1992).
Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in chloroform : methanol (20 : 1) and adding 1d HCl at room temperature.

Refinement
All H atoms were initially located in a difference map, but were constrained to an idealized geometry. Constrained bond lengths and isotropic displacement parameters: (C-H = 0.97 Å) and U iso (H) =1.2 U eq (C) for methylene, and (C-H = 0.93 Å) and U iso (H) =1.2U eq (C) for aromatic H atoms.

Special details
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.