Received 3 September 2013
The asymmetric unit of the title compound, C44H44N2O6, contains two independent molecules with similar conformations. The dihydronaphthalene ring systems are approximately planar [maximum deviations = 0.036 (2), 0.128 (2), 0.0.24 (2) and 0.075 (2) Å]. The dihedral angle between two dihydronaphthalene ring systems is 83.37 (4)° in one molecule and 88.99 (4)° in the other. The carbonyl O atom is linked with the adjacent hydroxy and imino groups via intramolecular O-HO and N-HO hydrogen bonds. In the crystal, molecules are linked through O-HO hydrogen bonds into layers parallel to (001), and adjacent layers are further stacked by - interactions between dihydronaphthalene and phenyl rings into a three-dimensional supramolecular architecture. In the crystal, one of the isopropyl groups is disordered over two positions with an occupancy ratio of 0.684 (8):0.316 (8).
For details of extraction and synthesis of gossypol and its derivatives, see: Kenar (2006). For synthesis and biological activities, see: Polsky et al. (1989); Radloff et al. (1985). For formation of crystalline forms of inclusion compounds, see: Ibragimov & Talipov (1999, 2004).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5738 ).
We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study F7-T048
Bruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA.
Ibragimov, B. T. & Talipov, S. A. (1999). J. Struct. Chem. 40, 686-704.
Ibragimov, B. T. & Talipov, S. A. (2004). Gossypol, in Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 606-614. New York: Dekker.
Kenar, J. A. (2006). J. Am. Oil Chem. Soc. 83, 269-303.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Polsky, B., Segal, S. J., Baron, P. A., Gold, J. W., Ueno, H. & Armstrong, D. (1989). Contraception, 39, 579-587.
Radloff, R. I., Deck, L. M., Royer, R. E. & Vander Jagt, D. L. (1985). Pharmacol. Res. Commun. 18, 1063-1073.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.