trans-1-Phenylpyrrolidine-2,5-dicarbonitrile

In the title compound, C12H11N3, the plane of the phenyl ring and the least-squares plane of the pyrrolidine ring enclose an angle of 14.30 (6)°. The intracyclic N atom features a nearly trigonal-planar coordination geometry due to π-interactions with the aromatic system. The pyrrolidine ring is present in a twist conformation for which the closest pucker descriptor is C9 T C8. Weak intermolecular C—H⋯N and C—H⋯π contacts occur

In the title compound, C 12 H 11 N 3 , the plane of the phenyl ring and the least-squares plane of the pyrrolidine ring enclose an angle of 14.30 (6) . The intracyclic N atom features a nearly trigonal-planar coordination geometry due to -interactions with the aromatic system. The pyrrolidine ring is present in a twist conformation for which the closest pucker descriptor is C9 T C8 . Weak intermolecular C-HÁ Á ÁN and C-HÁ Á Á contacts occur
The intracyclic nitrogen atom is nearly in the plane defined by the three carbon atoms bonded to it. The displacement of the nitrogen atom from the plane is only 0.073 (1) Å. The planarization of the nitrogen atom may be rationalized by possible π-interaction of the lone pair with the aromatic system.
The pyrrolidine ring is present in a twist-conformation for which the closest pucker descriptor is C9 T C8 [Cremer et al. (1975)]. This conformation is slightly distorted towards an envelope-conformation E C8 . In a related structure [Menezes et al. (2007)], the ring is twisted along the same bond, however, in the other direction ( C8 T C9 ).
Both carbonitrile nitrogen atoms act as acceptors in very weak contacts of the type C-H···N. Furthermore the packing features very weak C-H···π contacts with the phenyl π-system as acceptor. The packing of the title compound is shown in Figure 2.
supplementary materials sup-2 Refinement All H atoms were found in difference maps. The H atoms were positioned geometrically (bond distances for phenyl-CH: 0.95 Å, for aliphatic CH: 1.00 Å, for aliphatic CH 2 : 0.99 Å) and treated as riding on their parent atoms [U iso (H) = 1.2U eq (C)]. Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.