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(Pyrazinecarbonyl)hydrazones of heteroarenealdehydes: crystal structures formed from N—H···O, N—HN, C—H···O hydrogen-bonds, C—H···π and π···π interactions

✍ Scribed by Howie, R. Alan; da Silva Lima, Camilo H.; Kaiser, Carlos R.; da Silva, Marcele M.; de Souza, Marcos V. N.; Wardell, James L.; Wardell, Solange M. S. V.

Book ID
120330586
Publisher
Oldenbourg Wissenschaftsverlag
Year
2010
Tongue
English
Weight
398 KB
Volume
225
Category
Article
ISSN
2194-4946

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✦ Synopsis

Abstract

The molecules of the (pyrazinecarbonyl)hydrazones of the heterocyclic aldehydes RCHO with R = pyrrol-2-yl, furan-2-yl, thien-2-yl and pyridin-2-yl corresponding to compounds (2: X = NH), (2: X = O), (2: X = S)and 3, respectively, are formally rather similar. Despite this the molecular packing and intermolecular interactions show unexpectedly wide variation throughout the series. In 2 hydrogen-bonds link the planar molecules edge to edge to form chains or, in one case, planar ribbons while 3 exhibits zig-zag chain connectivity. Three-dimensional connectivity is attained by intermolecular hydrogen-bonds alone in ortho-(2: X = S), the orthorhombic polymorph of (2: X = S)and by intermolecular hydrogen-bonds combined with π···π interactions in (2: X = O) and 3. No more than two-dimensional layer connectivity is found in (2: X = NH) and the monoclinic polymorph, mono-(2: X = S) of (2: X = S).

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ÁC 6 H 3 N 2 O 5 À , there are NÐHÁ Á ÁO and CÐHÁ Á ÁO interactions which generate rings of motifs S(5), D, D 2 1 (4), R 1 2 (7), R 1 2 (5), R 2 1 (6), R 2 2 (10) and R 2 2 ( 14). The supramolecular aggregation is completed by the presence of CÐHÁ Á Á% and %±% interactions.