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2-Amino-6-[(2,6-dichlorophenyl)imino]-3-oxocyclohexa-1,4-dienecarbaldehyde

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Author(s): Cláudia M. B. Neves | José A. Fernandes | Mário M. Q. Simões | M. Graça P. M. S. Neves | José A. S. Cavaleiro | Filipe A. Almeida Paz

Journal: Acta Crystallographica Section E
ISSN 1600-5368

Volume: 67;
Issue: 11;
Start page: o3022;
Date: 2011;
Original page

ABSTRACT
The title compound, C13H8Cl2N2O2, was obtained by the oxidation of diclofenac {systematic name: 2-[2-(2,6-dichlorophenylamino)phenyl]acetic acid}, an anti-inflammatory drug, with hydrogen peroxide catalysed by chlorido[5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]manganese(III), using ammonium acetate as co-catalyst. The asymmetric unit contains two crystallographically independent molecules of the title compound (Z′ = 2). The close packing of individual molecules is mediated by a series of strong and rather directional N—H...Cl and N—H...O hydrogen bonds, plus weak π–π [distance between the individual double bonds of symmetry-related iminoquinone rings = 3.7604 (13) Å] and Cl...O interactions [3.0287 (18) Å].
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