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X-ray structure analyses of Smiles rearrangement and further cyclization products of 2-[3-cyanopropylthio(and oxy)]pyridine-3-carbonitriles revealed the structures of 5-amino-8-methyl-1,2-dihydrothieno[2,3-h][1,6]naphthyridine, C11H11N3S, and 5-amino-8-methyl-1,2-dihydrofuro[2,3-h][1,6]naphthyridine, C11H11N3O. The crystals of both compounds are isomorphous; monoclinic, space group P21/n. The molecules, related by a centre of symmetry, are linked through a N—H...N hydrogen bond. Common features of bond lengths and angles which characterize the thieno and furo[2,3-h][1,6]naphthyridine skeletons are described.

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Crystallographic Information File (CIF)
Contains datablocks text, II, III

CCDC references: 126291; 126292

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