Abstract
The title compound, C44H44N2O8, (systematic name: 1,1',6,6'-tetra-hydroxy-5,5'-diisopropyl-8,8'-bis-{[(4-meth-oxy-phen-yl)iminium-yl]meth-yl}-3,3'-dimethyl-2,2'-bi-naphthalene-7,7'-diolate) has been obtained by the addition of p-anizidine to gossypol dissolved in di-chloro-methane. In the solid state, the title compound exists in the enamine or quinoid form. The two naphthyl moieties are inclined to one another by 72.08 (5)°. The pendant phenyl rings are inclined at 22.26 (14) and 23.86 (13)° to the corresponding naphthyl rings. In the crystal, mol-ecules are incorporated into layers through inversion-related pairs of O-H⋯O inter-actions [graph sets R 2 (2)(20) and R 2 (2)(10)] and translation-related O-H⋯O inter-actions [graph set C(15)]. The packing of these layers in the crystal structure gives rise to channels in the [011] direction, with hydro-phobic inter-actions occurring between adjacent layers. The channels are 5-7 Å wide, and the void volume of each cell is 655 Å(3), corresponding to 26.6% of the cell volume. Disordered guest mol-ecules, probably solvent and water mol-ecules, occupy these voids of the crystal; their contribution to the scattering was removed with the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9-18] of PLATON [Spek (2009 ▸). Acta Cryst. D65, 148-155].
Highlights
The title compound, C44H44N2O8, (systematic name: 1,10,6,60 -tetrahydroxy-5,50 diisopropyl-8,80 -bis{[(4-methoxyphenyl)iminiumyl]methyl}-3,30 -dimethyl-2,20 binaphthalene-7,70 -diolate) has been obtained by the addition of p-anizidine to gossypol dissolved in dichloromethane
This interest has led to the synthesis and isolation of various gossypol derivatives, including many diamine-based gossypol Schiff bases
Gossypol and its Schiff base formed with aniline have been previously reported to form inclusion compounds with many small organic compounds (Beketov et al, 1994; Gdaniec et al, 1996; Talipov et al, 2004)
Summary
Gossypol [2,20 -bis(8-formyl-1,6,7-trihydroxy-5-isopropyl-3methylnaphthalene)] is a yellow pigment of cotton seeds (Adams et al, 1960). This compound was first isolated over 110 years ago (Marchlewski, 1899). Its study was initially important because the compound is associated with anti-nutritive or even toxic effects when cottonseed is overfed to animals. Antifertility (Coutinho, 2002) effects. This interest has led to the synthesis and isolation of various gossypol derivatives, including many diamine-based gossypol Schiff bases. We demonstrate that the Schiff base of gossypol with p-anizidine forms an open-channel structure when the compound is crystallized from solutions in dichloromethane. Symmetry codes: (i) x 1; y; z; (ii) x; y þ 1; z þ 1; (iii) x þ 1; y; z
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