Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 6 (June 2013)

organic compounds

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

hkldisplay filedownload file

Structure factor file (CIF format) (168.9 kbytes)
[ doi:10.1107/S0108270113010676/ov3028Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (172.8 kbytes)
[ doi:10.1107/S0108270113010676/ov3028IIsup3.hkl ]
Contains datablock II

hkldisplay filedownload file

Structure factor file (CIF format) (212.1 kbytes)
[ doi:10.1107/S0108270113010676/ov3028IIIsup4.hkl ]
Contains datablock III


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.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster