Acta Crystallographica Section C

Crystal Structure Communications

Volume 60, Part 8 (August 2004)

sq1162 scheme

Acta Cryst. (2004). C60, o559-o563 [doi:10.1107/S0108270104013812]

5-Acetyl-2-amino-6-methyl-4-(1-naphthyl)-4H-pyran-3-carbonitrile, methyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate and tert-butyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate

S. V. Nesterova, D. J. Wiedenfeld and V. N. Nesterov

Abstract: Syntheses and X-ray structural investigations have been carried out for the three title compounds, C₁₉H₁₆N₂O₂, (IIIa), C₁₉H₁₆N₂O₃, (IIIb), and C₂₂H₂₂N₂O₃, (IIIc), respectively. In molecules (IIIa) and (IIIc), the heterocyclic ring is practically flat, while in (IIIb) it adopts a flattened-boat conformation. In (IIIb) and (IIIc), the carbonyl group and a double bond of the heterocyclic ring are anti, but in (IIIa) they are syn and the carbonyl group participates in an intramolecular C-HO hydrogen bond which forms a six-membered ring. In molecules (IIIa) and (IIIc), the dihedral angles between the naphthalene substituent and the flat heterocyclic ring are 96.4 (3) and 102.6 (3)°, respectively. In (IIIb), the dihedral angle between the pseudo-axial naphthalene bicycle and the flat part of the pyran ring is 81.6 (3)°. In the crystal structure of (IIIa), intermolecular N-HN and N-HO hydrogen bonds link the molecules into a three-dimensional framework. In (IIIb) and (IIIc), only one H atom of the NH₂ group takes part in an N-HO hydrogen bond and infinite chains are formed along the a axis.

Formula: C₁₉H₁₆N₂O₂, C₁₉H₁₆N₂O₃ and C₂₂H₂₂N₂O₃

Online 10 July 2004


	Structure factor file (CIF format) (149.0 kbytes) Contains datablock IIIa

	Structure factor file (CIF format) (188.3 kbytes) Contains datablock IIIb

	Structure factor file (CIF format) (198.7 kbytes) Contains datablock IIIc

Notes:

To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.