N-p-Tolylpyrrolidine-1-carboxamide

In the title molecule, C12H16N2O, the pyrrolidine ring has a half-chair conformation. In the crystal, molecules are linked into C(4) chains along [001] by N—H⋯O hydrogen bonds.

In the title molecule, C 12 H 16 N 2 O, the pyrrolidine ring has a half-chair conformation. In the crystal, molecules are linked into C(4) chains along [001] by N-HÁ Á ÁO hydrogen bonds.

Related literature
For the medicinal properties of pyrrolidine compounds, see: Yang et al. (1997). For related structures, see: Kö hn et al.

Yu-Feng Li Comment
Pyrrolidine compounds have been shown to have medicinal properties (Yang et al., 1997). The crystal structure of the title compound is presented herein. The molecular structure of the title compound is shown in Fig. 1. The pyrrolidine ring has a half-chair conformation with atoms C10 and C11 forming the twist. In the crystal, the molecules are linked into chains along [001] by intermoecular N-H···O hydrogen bonds. The structures of related compounds have already been determined (Köhn et al., 2004;Li, 2011).

Experimental
A mixture of pyrrolidine (0.1 mol), and p-tolylcarbamic chloride (0.1 mol) was stirred in refluxing ethanol (20 ml) for 4 h to afford the title compound (0.068 mol, yield 68%). Colourless blocks of the title compound were obtained by recrystallization of a solution of the title compound in ethanol at room temperature.

Refinement
H atoms were fixed geometrically and allowed to ride on their attached atoms, with C-H distances = 0.93-0.97 Å; N-H = 0.86 Å and with U iso (H) = 1.2U eq (C,N) or 1.5U eq (C methyl ).  The molecular structure of the title compound showing 30% probability displacement ellipsoids.

N-p-Tolylpyrrolidine-1-carboxamide
Crystal data 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 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.