Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 12 (December 2005)

organic compounds

fg1879 scheme

Acta Cryst. (2005). C61, o741-o744 [doi:10.1107/S0108270105037078]

2-Amino-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile and 2-amino-4-(2-methoxyphenyl)-7,7-dimethyl-3-nitro-4,6,7,8-tetrahydro-5H-chromen-5-one hemihydrate

V. N. Nesterov, V. P. Kislyi, J. L. Sabutis, V. V. Nesterov, D. J. Wiedenfeld and V. V. Semenov

Abstract: Calculations of the conformational preferences of the methoxyphenyl substituent with respect to the pyran ring have been carried out for the two title compounds, C₁₉H₂₀N₂O₃, (II), and C₁₈H₂₀N₂O₅·0.5H₂O, (III). In both molecules, the heterocyclic ring adopts a flattened boat conformation and the fused cyclohexenone ring adopts a `sofa' conformation. The dihedral angles between these two flat fragments are 14.5 (1) and 9.3 (1)° in (II) and (III), respectively. In both molecules, the methoxy group of the pseudo-axial aryl substituent is syn with respect to the pyran ring. The dihedral angles between the 2-methoxyphenyl rings and the flat parts of the pyran rings are 86.3 (1) and 87.0 (1)°, respectively. In the crystal structure of (II), intermolecular N-HN and N-HO hydrogen bonds link molecules into a three-dimensional framework. In the crystal structure of (III), a strong intramolecular N-HO hydrogen bond links the flat conjugated H-N-C=C-N-O fragment into a six-membered ring. In (III), the water molecule lies on a twofold axis and forms bifurcated O-HO hydrogen bonds with the NO₂ group of the molecule. Also in (III), hydrogen bonds link the organic and water molecules into infinite tapes along the c axis.

Formula: C₁₉H₂₀N₂O₃ and C₁₈H₂₀N₂O₅·0.5H₂O


	Structure factor file (CIF format) (142.7 kbytes) Contains datablock II

	Structure factor file (CIF format) (152.1 kbytes) Contains datablock III

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