Acta Crystallographica Section C

Crystal Structure Communications

Volume 63, Part 12 (December 2007)

organic compounds

bm3039 scheme

Acta Cryst. (2007). C63, o685-o689 [ doi:10.1107/S0108270107049001 ]

Three sterically hindered 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate derivatives

V. N. Nesterov, D. J. Wiedenfeld, S. V. Nesterova and L. F. Hastings

Abstract: In the title compounds, 2-methoxyethyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate, C₂₁H₂₀N₂O₄, (II), isopropyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate, C₂₁H₂₀N₂O₃, (III), and ethyl 6-amino-5-cyano-2-methyl-4-(1-naphthyl)-4H-pyran-3-carboxylate, C₂₀H₁₈N₂O₃, (IV), the heterocyclic pyran ring adopts a flattened boat conformation. In (II) and (III), the carbonyl group and a double bond of the heterocyclic ring are mutually anti, but in (IV) they are mutually syn. The ester O atoms in (II) and (III) and the carbonyl O atom in (IV) participate in intramolecular C-HO contacts to form six-membered rings. The dihedral angles between the naphthalene substituent and the closest four atoms of the heterocyclic ring are 73.3 (1), 71.0 (1) and 74.3 (1)° for (II)-(IV), respectively. In all three structures, only one H atom of the NH₂ group takes part in N-HO [in (II) and (III)] or N-HN [in (IV)] intermolecular hydrogen bonds, and chains [in (II) and (III)] or dimers [in (IV)] are formed. In (II), weak intermolecular C-HO and C-HN hydrogen bonds, and in (III) intermolecular C-HO hydrogen bonds link the chains into ladders along the a axis.

Formula: C₂₁H₂₀N₂O₄, C₂₁H₂₀N₂O₃ and C₂₀H₁₈N₂O₃


	Structure factor file (CIF format) (176.2 kbytes) [ doi:10.1107/S0108270107049001/bm3039IIsup2.hkl ] Contains datablock II

	Structure factor file (CIF format) (173.0 kbytes) [ doi:10.1107/S0108270107049001/bm3039IIIsup3.hkl ] Contains datablock III

	Structure factor file (CIF format) (167.4 kbytes) [ doi:10.1107/S0108270107049001/bm3039IVsup4.hkl ] Contains datablock IV

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