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

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?? bonds, and ?-? stacking), leading to three-dimensional networks in each case, but with little similarity between them.

SUBMITTER: Cardoso LN

PROVIDER: S-EPMC5137586 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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

Cardoso Laura N F LN Noguiera Thais C M TC Kaiser Carlos R CR Wardell James L JL de Souza Marcus V N MV Lancaster Shaun T ST Harrison William T A WT

Acta crystallographica. Section E, Crystallographic communications 20161101 Pt 12

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 ...[more]

PMID: 27980808

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Different packing motifs of isomeric (E)-N'-(halo-phenyl-methyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazides controlled by C-H?O inter-actions.

Project description:The crystal structures of three isomeric (E)-N'-(chloro-phenyl-methyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazides (C14H13ClN2OS) are described, with the Cl atom in ortho (I), meta (III) and para (IV) positions in the benzene ring. The ortho-bromo derivative (II) (C14H13BrN2OS), which is isostructural with its chloro congener (I), is also reported. Mol-ecules (I)-(III) have similar conformations, which approximate to l-shapes, as indicated by their N-C-C-Ct (t = thio-phene) torsion angles of -90.1?(3), -91.44?(18) and -90.7?(9)°, respectively. The conformation of (IV) is different, with an equivalent torsion angle of -170.75?(11)° corresponding to a more extended shape for the mol-ecule. The thio-phene ring in each structure features 'flip' rotational disorder. The packing for (I) and (II) features inversion dimers, linked by pairs of C-H?O inter-actions, which generate R22(14) loops. In the crystal of (III), [010] C(8) chains arise, with adjacent mol-ecules linked by pairs of C-H?O hydrogen bonds. The packing for (IV) features unusually short C-H?O inter-actions arising from an H atom attached to the benzene ring (H?O = 2.18?Å), which lead to C(9) [301] chains. Hirshfeld fingerprint percentage contact contributions are similar for the four title compounds.

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