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Journal of Chemical Crystallography

, Volume 35, Issue 11, pp 917–922 | Cite as

Synthesis and X-ray structural investigations of 2-amino-7-methyl-4-(1-naphthyl)-5-oxo4H,5H-pyrano[4,3-b]pyran-3-carbonitrile and 2-amino-4-(1-naphthyl)-5-oxo-4H,5Hpyrano[3,2-c]chromene-3-carbonitrile

  • Vladimir N. Nesterov
  • David Wiedenfeld
  • Svitlana V. Nesterova
  • Lee M. Daniels
Article

Abstract

Synthesis and X-ray structural investigations have been carried out for the two title compounds C20H14N2O3 (4) and C23H14N2O3⋅C2H3N (5). Compound 4 crystallizes in the monoclinic space group P21/n, with a = 7.0542(5), b = 8.822(1), c = 24.833(2) Å, β = 94.30(4), V = 1541.0(4) Å3, and Z = 4. Compound 5 crystallizes with an acetonitrile solvent molecule in the monoclinic space group P21/n, with a = 11.075(1), b = 7.854(1), c = 22.703(2) Å, β = 90.67(1), V = 1974.5(3) Å3, and Z = 4. In both molecules, the 4H-pyran ring adopts a flattened-boat conformation. The naphthalene substituent occupies a pseudo-axial position and the dihedral angle with the flat part of the pyran ring is equal to 94.6(3) in 4 and 76.8(3) in 5. The mutual orientation of these fragments and the flatness of the heterocyclic rings lead to H⋅sH intramolecular steric interactions: H4A⋅sH18A 1.98 Å in 4 and 2.11 Å in 5. In the crystal of 4, intermolecular hydrogen bonds N–H⋅sO and C–H⋅sN link molecules into infinite tapes along the b axis. In the crystals of 5, intermolecular hydrogen bonds N–H⋅sO and C–H⋅sN link molecules into infinite layers parallel to the bc plane. In each case, the C–H⋅sN interaction can be considered to be a weak hydrogen bond. The acetonitrile molecules link via intermolecular weak C–H⋅sN hydrogen bonds to form infinite chains along the b axes.

Keywords

α,β-Unsaturated nitriles 4H-pyran crystal structure conjugation intermolecular H-bonds 

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Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  1. 1.Department of Natural SciencesNew Mexico Highlands UniversityLas VegasUSA
  2. 2.Rigaku/MSC, Inc.The WoodlandsUSA

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