Crystal structure of (9S,10S)-10-eth-oxy-9-hy-droxy-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetra-hydro-6H-benzo[c]chromen-1-yl 4-methyl-benzene-sulfonate

Waseem Gul; Ahmed Galal; Mahmoud A ElSohly; Paulo Carvalho

doi:10.1107/S2056989015024044

Crystal structure of (9S,10S)-10-eth-oxy-9-hy-droxy-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetra-hydro-6H-benzo[c]chromen-1-yl 4-methyl-benzene-sulfonate

Acta Crystallogr E Crystallogr Commun. 2015 Dec 24;71(Pt 12):o1082-3. doi: 10.1107/S2056989015024044. eCollection 2015 Dec 1.

Authors

Waseem Gul¹, Ahmed Galal², Mahmoud A ElSohly³, Paulo Carvalho⁴

Affiliations

¹ National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA; El Sohly Laboratories Inc., 5 Industrial Park Drive, Oxford, MS 38655, USA.
² National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA.
³ El Sohly Laboratories Inc., 5 Industrial Park Drive, Oxford, MS 38655, USA; National Center for Natural Products Research, Department of Pharmaceutics, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
⁴ School of Pharmacy, Notre Dame of Maryland University, 4701 North Charles Street, 21210, Baltimore, MD, USA.

Abstract

In the structure of the title compound, C30H40O6S, the cyclo-hexene and heterocyclic rings are linked by a double bond. The cyclo-hexene ring has a half-chair conformation (the methyl-ene group adjacent to the hy-droxy substituent lies above the remaining atoms) and the hy-droxy and eth-oxy groups have equatorial and bis-ectional dispositions, respectively. The heterocyclic ring has an envelope conformation (with the CMe2 C atom being the flap). The dihedral angle between the aromatic rings is 53.88 (10)°. A long intra-molecular C-H⋯S inter-action is noted. In the mol-ecular packing, hy-droxy-O-H⋯O(sulfonate) hydrogen bonds lead to a helical chain along [010]. Connections between chains are of the type methyl-C-H⋯O(sulfonate) and lead to supra-molecular layers that lie parallel to (001). The studied crystal was an inversion twin.

Keywords: crystal structure; hydrogen bonding; photooxygenation; Δ9–THC tosylate.