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

ABSTRACT: 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?Å). The carboximide N atom and the five C atoms of the 2-methyl-prop-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 =CH(2) group of the vinyl fragment towards the naphthalimide rings, giving the mol-ecule 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)?Å. 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 mol-ecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C-H?O contacts of varying strength, which stack the mol-ecules down the b axis.

SUBMITTER: Hanton LR

PROVIDER: S-EPMC2979536 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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

Hanton Lyall R LR Moratti Stephen C SC Shi Zheng Z Simpson Jim J

Acta crystallographica. Section E, Structure reports online 20100529 Pt 6

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 Å). The carboximide N atom and the five C atoms of the 2-methyl-prop-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 =CH(2) group of the vinyl fragment towards the naphthalimide rings, giving the mol-ecule an extended configuration. The piperidine ring adopts a c ...[more]

PMID: 21579543

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