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C—H...O and C—H...N interactions in three hexahydrocycloocta[ b ]pyridine‐3‐carbonitriles
Author(s) -
Vishnupriya R.,
Suresh J.,
Maharani S.,
Kumar R. Ranjith
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229614000291
Subject(s) - pyridine , chemistry , ring (chemistry) , substituent , alkoxy group , stereochemistry , molecule , intermolecular force , aryl , supramolecular chemistry , crystallography , crystal structure , medicinal chemistry , alkyl , organic chemistry
The structures of three new pyridine derivatives, 2‐methoxy‐4‐(4‐methoxyphenyl)‐5,6,7,8,9,10‐hexahydrocycloocta[ b ]pyridine‐3‐carbonitrile, C 20 H 22 N 2 O 2 , (I), 2‐ethoxy‐4‐(3‐nitrophenyl)‐5,6,7,8,9,10‐hexahydrocycloocta[ b ]pyridine‐3‐carbonitrile, C 20 H 21 N 3 O 3 , (II), and 2‐ethoxy‐4‐(4‐methoxyphenyl)‐5,6,7,8,9,10‐hexahydrocycloocta[ b ]pyridine‐3‐carbonitrile, C 21 H 24 N 2 O 2 , (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.