Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 6 (June 2013)


organic compounds



ov3028 scheme

Acta Cryst. (2013). C69, 642-646    [ doi:10.1107/S0108270113010676 ]

N-H...O and N-H...N interactions in three pyran derivatives

R. Vishnupriya, J. Suresh, S. Sivakumar and R. R. Kumar

Abstract: The three pyran structures 6-methylamino-5-nitro-2,4-diphenyl-4H-pyran-3-carbonitrile, C19H15N3O3, (I), 4-(3-fluorophenyl)-6-methylamino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile, C19H14FN3O3, (II), and 4-(4-chlorophenyl)-6-methylamino-5-nitro-2-phenyl-4H-pyran-3-carbonitrile, C19H14ClN3O3, (III), differ in the nature of the aryl group at the 4-position. The heterocyclic ring in all three structures adopts a flattened boat conformation. The dihedral angle between the pseudo-axial phenyl substituent and the flat part of the pyran ring is 89.97 (1)° in (I), 80.11 (1)° in (II) and 87.77 (1)° in (III). In all three crystal structures, a strong intramolecular N-H...O hydrogen bond links the flat conjugated H-N-C=C-N-O fragment into a six-membered ring. In (II), molecules are linked into dimeric aggregates by N-H... O(nitro) hydrogen bonds, generating an R22(12) graph-set motif. In (III), intermolecular N-H...N and C-H...N hydrogen bonds link the molecules into a linear chain pattern generating C(8) and C(9) graph-set motifs, respectively.

Formula: C19H15N3O3, C19H14FN3O3 and C19H14ClN3O3


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Chemical Markup Language (CML) file (6.3 kbytes)
[ doi:10.1107/S0108270113010676/ov3028Isup5.cml ]
Supplementary material


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Chemical Markup Language (CML) file (6.4 kbytes)
[ doi:10.1107/S0108270113010676/ov3028IIsup6.cml ]
Supplementary material


cmldisplay filedownload file

Chemical Markup Language (CML) file (6.4 kbytes)
[ doi:10.1107/S0108270113010676/ov3028IIIsup7.cml ]
Supplementary material


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