Acta Crystallographica Section C

Crystal Structure Communications

Volume 62, Part 4 (April 2006)

organic compounds

hj1088 scheme

Acta Cryst. (2006). C62, o173-o177 [ doi:10.1107/S0108270106005026 ]

(Z)-4-(2,6-Dichlorophenyldiazenyl)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxycyclohexa-2,4-dienone and the 3-methoxyphenyldiazenyl and 4-methoxyphenyldiazenyl analogues

A. Özek, C. Albayrak, M. Odabasoglu and O. Büyükgüngör

Abstract: The title compounds, (Z)-4-(2,6-dichlorophenyldiazenyl)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxycyclohexa-2,4-dienone, C₁₈H₁₉Cl₂N₃O₅, (I), (Z)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxy-4-(3-methoxyphenyldiazenyl)cyclohexa-2,4-dienone, C₁₉H₂₃N₃O₆, (II), and (Z)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxy-4-(4-methoxyphenyldiazenyl)cyclohexa-2,4-dienone, C₁₉H₂₃N₃O₆, (III), all adopt the keto-amine tautomeric form, and the hydroxy H atoms are located on the N atom in all three compounds. Strong intramolecular N-HO hydrogen bonds arise as a result of the shifts achieved by the hydroxy H atoms of the Schiff bases to the N atoms. Positional disorder was observed in molecules (II) and (III). In all three compounds, C-H [pi] and [pi] - [pi] interactions affect the packing of the molecules. The compounds exhibit trans geometry with respect to the azo N=N double bond, and the molecules are linked by O-HO hydrogen bonds to form three-dimensional networks.

Formula: C₁₈H₁₉Cl₂N₃O₅, C₁₉H₂₃N₃O₆ and C₁₉H₂₃N₃O₆


	Structure factor file (CIF format) (181.7 kbytes) [ doi:10.1107/S0108270106005026/hj1088Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (179.8 kbytes) [ doi:10.1107/S0108270106005026/hj1088IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (178.4 kbytes) [ doi:10.1107/S0108270106005026/hj1088IIIsup4.hkl ] Contains datablock III

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