Abstract
In the title compound, C21H20N2O3, the naphthalimide unit is almost planar (r.m.s. deviation for the 15 non-H atoms = 0.059 Å). 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 Å), which subtends an angle of 84.34 (7)° to the naphthalamide plane. This orients the =CH2 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—Npip bond length being 1.404 (4) Å. In the crystal structure, π–π contacts with centroid–centroid distances of 3.5351 (18) and 3.7794 (18) Å supported by C—H⋯O hydrogen bonds link adjacent molecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C—H⋯O contacts of varying strength, which stack the molecules down the b axis.
Highlights
In the title compound, C21H20N2O3, the naphthalimide unit is almost planar
3.5351 (18) and 3.7794 (18) Å supported by C—H O
C—H O contacts of varying strength, which stack the molecules down the b axis
Summary
Key indicators: single-crystal X-ray study; T = 90 K; mean (C–C) = 0.005 Å; R factor =. 2-methylprop-2-enoyl substituent lie in a plane (r.m.s. deviation = 0.009 Å), which subtends an angle of 84.34 (7) to the naphthalamide plane. Deviation = 0.009 Å), which subtends an angle of 84.34 (7) to the naphthalamide plane This orients the CH2 group of the vinyl fragment towards the naphthalimide rings, giving the molecule an extended configuration. In the crystal structure, – contacts with centroid–centroid distances of. 3.5351 (18) and 3.7794 (18) Å supported by C—H O hydrogen bonds link adjacent molecules in a head-to-tail fashion, forming dimers. C—H O contacts of varying strength, which stack the molecules down the b axis
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