Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 2 (February 2014)


computational materials discovery



ov3043 scheme

Acta Cryst. (2014). C70, 236-240    [ doi:10.1107/S2053229614000291 ]

C-H...O and C-H...N inter­actions in three hexa­hydro­cyclo­octa­[b]pyridine-3-carbo­nitriles

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

Abstract: The structures of three new pyridine derivatives, 2-meth­oxy-4-(4-meth­oxy­phenyl)-5,6,7,8,9,10-hexa­hydro­cyclo­octa­[b]pyridine-3-carbo­nitrile, C20H22N2O2, (I), 2-eth­oxy-4-(3-nitrophenyl)-5,6,7,8,9,10-hexa­hydro­cyclo­octa­[b]pyridine-3-carbonitrile, C20H21N3O3, (II), and 2-eth­oxy-4-(4-meth­oxy­phenyl)-5,6,7,8,9,10-hexa­hydro­cyclo­octa­[b]pyridine-3-carbo­nitrile, C21H24N2O2, (III), differ in the nature of the substituents either at the 2-position of the central pyridine ring or on the pendent aryl ring. This simple change in the structure substantially alters the inter­molecular inter­action patterns. The substituted phenyl group adopts a synclinal geometry with respect to the plane of the pyridine ring in all three compounds. In (I), a C-H...N inter­action results in a one-dimensional chain parallel to the b axis. In (II), there are two C-H...N(nitrile) inter­actions from different symmetry-related mol­ecules, resulting in a two-dimensional network parallel to the bc plane. There is also a weak C-H...O inter­action from the eth­oxy group to an adjacent nitro O atom. The present work is an example of how the simple replacement of a substituent in the main mol­ecular scaffold may transform the structure type, paving the way for a variety of supra­molecular motifs and consequently altering the complexity of the inter­molecular inter­action patterns.

Formula: C20H22N2O2, C20H21N3O3 and C21H24N2O2

Keywords: crystal structure; cyclo­alkeno­pyridine structures; hydrogen bonding.


hkldisplay filedownload file

Structure factor file (CIF format) (159.2 kbytes)
[ doi:10.1107/S2053229614000291/ov3043Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (163.3 kbytes)
[ doi:10.1107/S2053229614000291/ov3043IIsup3.hkl ]
Contains datablock II


hkldisplay filedownload file

Structure factor file (CIF format) (168.3 kbytes)
[ doi:10.1107/S2053229614000291/ov3043IIIsup4.hkl ]
Contains datablock comp3


Notes:

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