N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide

In the title compound, C(21)H(20)N(2)O(3), the naphthalimide unit is almost planar (r.m.s. deviation for the 15 non-H atoms = 0.059 angstrom). The carboximide N atom and the five C atoms of the 2-methylprop-2-enoyl substituent also lie in a plane (r.m.s. deviation = 0.009 angstrom), which subtends an angle of 84.34 (7)degrees to the naphthalamide plane. This orients the =CH(2) group of the vinyl fragment towards the naphthalimide rings, giving the molecule an extended configuration. The piperidine ring adopts a chair conformation and there is evidence for some delocalization between the naphthalene and piperidine units, the C-N(pip) bond length being 1.404 (4) angstrom. In the crystal structure, pi-pi contacts with centroid-centroid distances of 3.5351 (18) and 3.7794 (18) angstrom supported by C-H center dot center dot center dot O hydrogen bonds link adjacent molecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C-H center dot center dot center dot O contacts of varying strength, which stack the molecules down the b axis.