Crystal structure of rac-(3a′R,9a′R)-3a′-(indol-3-yl)-1′,2′,3′,3a′,4′,9a′-hexahydrospiro[cyclopentane-1,9′-pentaleno[1,2-b]indole] p-xylene hemisolvate

Wayland E. Noland, Matthew A. Worth, Andrew K Schneerer, Courtney L. Paal, Kenneth J. Tritch, H. Stoeckli-Evans

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The title compound, C26H26N2·0.5C8H10, is the first reported characterized 2:2 product from acid-catalyzed condensation of indole with cyclopentanone and no other 2:2 products were observed. Recrystallization from p-xylene gave the title hemisolvate with the p-xylene molecule located about an inversion center. The terminal pentalene ring is envelope-flap disordered at the C atom farthest from the skeletal indole unit, with a refined occupancy ratio of 0.819 (4):0.181 (4). The major component has this C atom bent away from the spiro-fused cyclopentane ring. In the crystal, molecules are connected by N - H⋯π interactions, forming chains along [100], and N - H⋯π and C - H⋯π interactions, forming chains along [001], which results in the formation of slabs parallel to (010).

Original languageEnglish (US)
Pages (from-to)516-519
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number5
DOIs
StatePublished - May 1 2015

Keywords

  • Annulation
  • Crystal structure
  • Cyclic ketone
  • Disorder
  • Indole
  • X - H⋯π interactions

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