Different weak inter-actions in the crystals of three isomeric (E)- N-methyl- N'-(nitro-benzyl-idene)-2-(thio-phen-2-yl)acetohydrazides

Laura N F Cardoso; Thais C M Noguiera; Carlos R Kaiser; James L Wardell; Marcus V N de Souza; Shaun T Lancaster; William T A Harrison

doi:10.1107/S2056989016016856

Different weak inter-actions in the crystals of three isomeric (E)- N-methyl- N'-(nitro-benzyl-idene)-2-(thio-phen-2-yl)acetohydrazides

Acta Crystallogr E Crystallogr Commun. 2016 Nov 1;72(Pt 12):1677-1682. doi: 10.1107/S2056989016016856. eCollection 2016 Dec 1.

Authors

Laura N F Cardoso¹, Thais C M Noguiera², Carlos R Kaiser³, James L Wardell⁴, Marcus V N de Souza², Shaun T Lancaster⁵, William T A Harrison⁵

Affiliations

¹ Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-FarManguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, Brazil; Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, Rio de Janeiro, Brazil.
² Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-FarManguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, Brazil.
³ Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, Rio de Janeiro, Brazil.
⁴ Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-FarManguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, Brazil; Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.
⁵ Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.

Abstract

The crystal structures of three isomeric (E)-N-methyl-N'-(nitro-benzyl-idene)-2-(thio-phen-2-yl)acetohydrazides (formula C₁₄H₁₃N₃O₃S) are described, with the nitro group in ortho, meta and para positions in the benzene ring. In each crystal structure, mol-ecules are linked by various weak inter-actions (C-H⋯O and C-H⋯π bonds, and π-π stacking), leading to three-dimensional networks in each case, but with little similarity between them.

Keywords: carbohydrazide; crystal structure; methylation; weak hydrogen bonds.