Research Article: 3,5a,9-Trimethyl-8-(2-phenylhydrazin-1-ylidene)-4,5,5a,9b-tetrahydro-3aH,8H-naphtho[1,2-b]furan-2(3H)-one

Date Published: July 01, 2012

Publisher: International Union of Crystallography

Author(s): Sammer Yousuf, Syed M. Younas, Nida Ambreen, Khalid M. Khan, Ghulam A. Miana.


The title compound, C21H24N2O2, is a phenyl hydrazine derivative of the well known anthelminthic agent α-santonin, which is composed of three fused rings (benzodieneone, cyclo­hexane and γ-lactone). The cyclo­hexa­dienone ring adopts a boat conformation, the cyclo­hexane ring is in a chair conformation and the trans-fused γ-lactone ring adopts a C-envelope conformation. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming chains along the a axis.

Partial Text

For the isolation of α-santonin, see: Kahler (1830 ▶). For the crystal structure and stereochemistry of α-santonin, see: White & Sim (1975 ▶); Coggon & Sim (1969 ▶). For puckering parameters, see: Cremer & Pople (1981 ▶).




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