Abstract
On the basis of a measurement of the frequencies and intensities of the stretching vibrations of the amino, amido, and ester groups in the IR spectra, it was established that products of the reaction of N-benzenesulfonylhydroxynaphthalimides with ammonia in alcohol solutipns have a structure of the type of 1-carbamoylbenz[c,d]-indol-2-ones and are not molecules with a seven-membered heterocycle, by analogy with 3-oxido-2-alkylnaphtho[1,8-d,e][1,3] oxoniazepin-1-ones. A determination of the molecular and crystal structure of one of these compounds (C13H10N2O2) confirmed this conclusion: The molecule is 1-(N-methylcarbamoyl)benz[c,d]indol-2-one. In the naphthalene ring of the molecule the bond angles at the central bond are deformed analogously to that found in acenaphthene. The intramolecular hydrogen bond O···HN closes a six-membered ring in the molecule. The crystal is constructed from dimers formed by intermolecular hydrogen bonds O···HN.
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