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Crystal and Molecular Structure of 6,6′-Dimethoxy-gossypol:Acetic acid (1:1)

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Abstract

By crystallization from dilute solutions of acetic acid (2–4%) in diethyl ether, acetone, or methyl ethyl ketone, 6,6′-dimethoxy-gossypol forms a solvate with acetic acid in a one-to-one molar ratio. The compound crystallizes in the triclinic P \( \overline{1} \) space group and has unit cell dimensions of a = 7.5793(10) Å, b = 14.7211(19) Å and c = 14.740(2) Å, α = 106.260(3)°, β = 102.310(3)°, γ = 95.975(3)°, Z = 2. The structure was solved by direct methods and refined to an R1 value of 0.0394 on 4252 observed reflections. Enantiomeric pairs of dimethoxy-gossypol molecules form centrosymmetic dimers that are characterized by a pair of intermolecular hydrogen bonds and by hydrophobic stacking between pairs of naphthalene rings. The acetic acid molecule accepts a hydrogen bond from a gossypol hydroxyl group and donates to a hydrogen bond with one of the aldehyde groups of an adjacent gossypol molecule. Although there is less hydrogen bonding in this structure than in the gossypol:acetic acid (1:1) structure, the molecular packing of the two compounds is similar.

Graphical abstract

Crystal and molecular structure of 6,6′-dimethoxy-gossypol:acetic acid (1:1)

Michael K. Dowd and Edwin D. Stevens

The molecular structure of the acetic acid solvate of 6,6′-dimethoxy-gossypol is presented.

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Acknowledgments

The authors thank Cotton Inc. for funding (Project 05-581) and J. Scheffler (ARS, Stoneville, MS) for providing laboratory space for growing crystals.

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Authors and Affiliations

  1. Southern Regional Research Center, ARS, USDA, 1100 Robert E. Lee Blvd., New Orleans, LA, 70124, USA

    Michael K. Dowd

  2. Department of Chemistry, University of New Orleans, 2000 Lakefront Drive, New Orleans, LA, 70148, USA

    Edwin D. Stevens

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  1. Michael K. Dowd
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  2. Edwin D. Stevens
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Correspondence to Michael K. Dowd.

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Dowd, M.K., Stevens, E.D. Crystal and Molecular Structure of 6,6′-Dimethoxy-gossypol:Acetic acid (1:1). J Chem Crystallogr 37, 765–770 (2007). https://doi.org/10.1007/s10870-007-9247-0

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  • DOI: https://doi.org/10.1007/s10870-007-9247-0

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