2-{[Tris(hydroxymethyl)methyl]amino-methylene}cyclohexa-3,5-dien-1(2H)-one and its 6-hydroxy and 6-methoxy derivatives

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Odabasoglu M., Albayrak C., Buyukgungor O., Lonnecke P.

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, vol.59, 2003 (SCI-Expanded)

• Publication Type: Article / Article
• Volume: 59
• Publication Date: 2003
• Doi Number: 10.1107/s0108270103020997
• Journal Name: ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED)
• Ondokuz Mayıs University Affiliated: No

Abstract

The title compounds, 2-{[tris(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one, C11H15NO4, (I), 6-hydroxy-2-{[tris (hydroxymethyl)methyl] aminomethylene}-cyclohexa-3,5-dien-1(2H)-one, C11H15NO5, (II), and 6-methoxy-2-{[tris(hydroxymethyl)methyl] aminomethylene}cyclohexa-3,5-dien-1(2H)-one, C12H17NO5, (III), adopt the ketoamine tautomeric form, with the formal hydroxy H atom located on the N atom, and the NH group and oxo O atom display a strong intramolecular N-H...O hydrogen bond. The N-H...O hydrogen-bonded rings are almost planar and coupled with the cyclohexadiene rings. The carbonyl O atoms accept two other H atoms from the alcohol groups of adjacent molecules in (I), and one from the alcohol and one from the phenol group in (II), but from only one alcohol H atom in (III).