caa a22 4500 463185099 CHVBK 20180406164850.0 cr unu---uuuuu 170326e20071101xx s 000 0 eng 10.1007/s10870-007-9247-0 doi (NATIONALLICENCE)springer-10.1007/s10870-007-9247-0 Crystal and Molecular Structure of 6,6′-Dimethoxy-gossypol:Acetic acid (1:1) [Elektronische Daten] [Michael Dowd, Edwin Stevens] 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. Springer Science+Business Media, LLC, 2007 Clathrate nationallicence Gossypol nationallicence H-clathrate nationallicence Natural product nationallicence Solvate nationallicence X-ray structure nationallicence Dowd Michael Southern Regional Research Center, ARS, USDA, 1100 Robert E. Lee Blvd., 70124, New Orleans, LA, USA aut Stevens Edwin Department of Chemistry, University of New Orleans, 2000 Lakefront Drive, 70148, New Orleans, LA, USA aut Journal of Chemical Crystallography Springer US; http://www.springer-ny.com 37/11(2007-11-01), 765-770 1074-1542 37:11<765 2007 37 10870 https://doi.org/10.1007/s10870-007-9247-0 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10870-007-9247-0 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Dowd Michael Southern Regional Research Center, ARS, USDA, 1100 Robert E. Lee Blvd., 70124, New Orleans, LA, USA aut NATIONALLICENCE 700 1- Stevens Edwin Department of Chemistry, University of New Orleans, 2000 Lakefront Drive, 70148, New Orleans, LA, USA aut NATIONALLICENCE 773 0- Journal of Chemical Crystallography Springer US; http://www.springer-ny.com 37/11(2007-11-01), 765-770 1074-1542 37:11<765 2007 37 10870 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer