(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

Abstract

The title compounds, (Z)-4-(2,6-dichlorophenyldiazenyl)-6-{[1,3-dihydroxy- 2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxycyclohexa-2,4-dienone, C<inf>18</inf>H<inf>19</inf>Cl<inf>2</inf>N<inf>3</inf>O<inf>5</inf>, (I), (Z)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]-methylene} -2-methoxy-4-(3-methoxyphenyldiazenyl)cyclohexa-2,4-dienone, C <inf>19</inf>H<inf>23</inf>N<inf>3</inf>O<inf>6</inf>, (II), and (Z)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene} -2-methoxy-4-(4-methoxyphenyldiazenyl)cyclohexa-2,4-dienone, C <inf>19</inf>H<inf>23</inf>N<inf>3</inf>O<inf>6</inf>, (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 - H ⋯ O 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 ⋯ π and π-π 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 - H ⋯ O hydrogen bonds to form three-dimensional networks. © 2006 International Union of Crystallography.