N-(2-Pyridylmethyl)phthalimide

In the title compound, C14H10N2O2, the phtalimide and 2-pyridylmethyl units are almost perpendicular, with an interplanar angle of 85.74 (2)°. In the crystal, molecules are linked by weak C—H⋯O interactions, forming chains running along the b axis. The packing is further stabilized by offset π–π interactions between adjacent pyridine rings, with a centroid–centroid distance of 3.855 (2) Å.

In the title compound, C 14 H 10 N 2 O 2 , the phtalimide and 2pyridylmethyl units are almost perpendicular, with an interplanar angle of 85.74 (2) . In the crystal, molecules are linked by weak C-HÁ Á ÁO interactions, forming chains running along the b axis. The packing is further stabilized by offsetinteractions between adjacent pyridine rings, with a centroidcentroid distance of 3.855 (2) Å .

Comment
Phthalimides are indispensable in protection and deprotection of primary amines (Ing & Manske, 1926;Gibson & Bradshaw, 1968;Ishii & Sakaguchi, 2004). Phthalimide derivatives are useful in photochemical synthesis (Yoon & Mariano, 2001) and catalytic reactions (Huang et al., 2006;Rodríguez et al., 2006). Some of the phthalimide derivatives have applications as drugs (Vamecq et al., 2000). Thus, they have been used as novel biological modifiers for tumor necrosis (Miyachi et al., 1997). Their fluorescence properties are highly environment sensitive (Vázquez et al., 2005) and find application as biological probes. In our ongoing research on phthalimides as intermediates in supramolecular host design, we have synthesized the title compound, (I).
In (I), all bond lengths and angles show normal values. The phtalimide and 2-pyridylmethyl moieties are almost pependicular with an interplanar angle of 85.74° ( Fig.1).

Experimental
A solution of 2-aminomethyl-pyridine (1 g, 9.25 mmol) in dimethylformamide(DMF) (5 ml) was added dropwise to (1.36 g, 9.18 mmol) of phthalic anhydride dissolved in 10 ml of DMF and refluxed for 6 h. The resulting solution was concentrated under reduced pressure to a viscous yellow liquid. Addition of water (25 ml) gave a colorless solid which was recovered by filtration and dried under vacuum. The product was recrystallized from ethanol to give suitable crystals for X-ray diffraction analysis (m.p. 399 K)

Refinement
Non-hydrogen atoms were refined anisotropically. Aromatic and methylene H atoms were positioned geometrically and constrained using the riding-model approximation [C-H aryl = 0.93 Å, U iso (H aryl ) = 1.2 U eq (C aryl ); C-H methylene = 0.97 Å, U iso (H methylene ) = 1.2 U eq (C methylene )], but the coordinates were refined freely.  Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius.