Research Article: (3aR*,6S*,7aR*)-7a-Chloro-6-methyl-2-(4-methyl­phenyl­sulfon­yl)-2,3,3a,6,7,7a-hexa­hydro-3a,6-ep­oxy-1H-isoindole

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Ersin Temel, Aydın Demircan, Gözde Beyazova, Orhan Büyükgüngör.


In the title compound, C16H18ClNO3S, the six-membered ring has a boat conformation. The two five-membered rings with the bridging O atom adopt envelope conformations, whereas the N-containing five-membered ring adopts a twisted conformation. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network.

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For background to the intra­molecular Diels–Alder reaction with furan (IMDAF) as diene partner, see: Lipshutz (1986 ▶); Heiner et al. (1996 ▶); Prajapati et al. (2000 ▶); Kappe et al. (1997 ▶); Padwa et al. (1997 ▶). For our studies of the intra­molecular free radical reaction of furan with a carbon side chain, see: Demircan & Parsons (1998 ▶, 2002 ▶); Demircan et al. (2006 ▶); Karaarslan et al. (2007 ▶). For our investigation of whether the protective group on nitro­gen influences the cyclo­addition process, see: Koşar et al. (2006 ▶); Arslan et al. (2008 ▶); Temel et al. (2011 ▶); Demircan et al. (2011 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).