Acta Crystallographica Section E

Structure Reports Online

Volume 68, Part 12 (December 2012)

organic compounds

Acta Cryst. (2012). E68, o3278    [ doi:10.1107/S1600536812044194 ]


M. Mojzych, Z. Karczmarzyk and A. Fruzinski

Abstract: The title compound, C21H16N4, obtained under standard Suzuki cross-coupling conditions, is a model compound in the synthesis and biological activity evaluation of new aza-analogues of sildenafil containing a pyrazolo­[4,3-e][1,2,4]triazine system. An N-H...N intra­molecular hydrogen bond involving the amino­benzene system and the 1,2,4-triazine moiety helps to establish a near coplanar orientation of the rings with a dihedral angle of 12.04 (4)°, which is believed to be necessary for the biological activity of sildenafil analogues. The 1,2,4-triazine ring is slightly distorted from planarity [r.m.s deviation = 0.0299 (11) Å] and forms dihedral angles of 58.60 (4) and 36.35 (3)° with the pendant phenyl rings. The crystal packing features bifurcated N-H...(N,N) hydrogen bonds linking screw-axis-related mol­ecules into chains parallel to the [010] direction and [pi]-[pi] inter­actions, with a centroid-centroid separation of 3.8722 (7) Å and a slippage of 1.412 (3) Å. The crystal studied was a nonmerohedral twin with a ratio of 0.707 (2):0293 (2).

htmldisplay filedownload file

Hyper-Text Markup Language (HTML) file
[ doi:10.1107/S1600536812044194/lr2082sup0.html ]
Supplementary materials

cmldisplay filedownload file

Chemical Markup Language (CML) file
[ doi:10.1107/S1600536812044194/lr2082Isup3.cml ]
Supplementary material


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