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Synthesis, characterization and crystal structures of the bidentate Schiff base N,N'-bis­(2-nitro­cinnamaldehyde)­ethyl­enedi­amine and its complex with CuNCS and tri­phenyl­phosphane

Lookup NU author(s): Professor William Clegg, Dr Ross Harrington, Professor Mohammad Habibi

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Abstract

Reaction of copper(I) thiocyanate and triphenylphosphine with the bidentate Schiff base N,N'-bis(trans-2-nitrocinnamaldehyde) ethylenediamine [Nca2en, 1, IUPAC name (1E,1'E,2E,2'E)-N,N'-(ethane-1,2-diyl)bis(3-(2-nitrophenyl)- prop-2-en-1-imine)] in a 1:1:1 molar ratio in acetonitrile resulted in the formation of the complex [Cu(NCS)(Nca2en) (PPh3)] [2, (1E,1'E,2E,2'E)-N,N'-{(ethane-1,2-diyl)bis(3-(2-nitrophenyl)prop-2-en-1-imine)}(thiocyanate-κN)(triphenylphosphine) copper]. The ligand and complex have been characterized by elemental analyses, IR, electronic and 1H NMR spectroscopy, and X-ray crystallography. The molecule of Nca2en lies on a crystallographic inversion centre, with a trans conformation for the ethylenediamine unit and displays significant twists from coplanarity of its nitro, aromatic ring, conjugated chain, and especially ethylenediamine segments. It acts as a bidentate ligand coordinating via two N atoms to the copper atom in the complex 2, in which the ethylenediamine unit necessarily adopts a somewhat flattened gauche conformation, resulting in a rather bowed shape overall for the ligand. The NCS- ligand is coordinated through its N atom. The geometry around the copper atom is distorted tetrahedral with a small N–Cu–N bite angle of 81.56 (12)° and an enlarged opposite angle of 117.29 (9)° for SCN–Cu–P. Comparisons are made with the analogous Schiff base having no nitro substituents and with metal complexes of both ligands.

Publication metadata

Author(s): Clegg W, Harrington RW, Barati K, Habibi MH, Montazerozohori M, Lalegani A

Publication type: Article

Publication status: Published

Journal: Acta Crystallographica, Section C

Year: 2015

Volume: 71

Issue: 7

Pages: 578-583

Online publication date: 01/07/2015

Acceptance date: 04/06/2015

Date deposited: 03/06/2015

ISSN (electronic): 2053-2296

Publisher: Wiley-Blackwell

URL: http://dx.doi.org/10.1107/S2053229615010815

DOI: 10.1107/S2053229615010815

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