Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 2 (February 2014)

organic compounds

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.

CCDC references: 980061, 980062 and 980063

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

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


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