(rac-5RS,7RS,8SR)-Spiro[7-methoxycarbonyl-1-aza-3-thiabicyclo[3.3.0]octane-8,1′-acenaphthylen]-2′-one

Abstract

The title compound, C19H17NO3S, crystallizes in the monoclinic space group P21/c, with four mol­ecules in the unit cell. The structure contains a spiro‐carbon connecting a bi­cyclo‐octane group, consisting of two fused five‐membered rings, to an ace­naphthyl­ene moiety. The five‐membered ring containing the S atom is in an envelope conformation. The conformation of the other five‐membered ring of the bi­cyclo‐octane moiety is close to a half‐chair. The methoxycarbonyl group is equatorially substituted.

Spectral Analysis and Crystal Structure of Spiro[2.2”] Acenaphthene-1”-One-Spiro[3.3’]-5’-(2,3-Dichlorophenyl Methylidene)-1’-Methylpiperidin-4’-One-4- (2,3-Dichlorophenyl) Octahydroindolizine

“…As a result of these steric repulsions, the bond angle C3C31C32 expands to 128.69 ( . These values are in agreement with related structures [20][21][22][23][24]. The C8-N2 bond distance being 1.450 (3) Å is comparable to the C sp 2 -N sp 2 distances found in similar structures [25,26].…”

5′′-(2,4-Dichlorobenzylidene)-1′-(2,4-dichlorophenyl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a'-octahydrodispiro[acenaphthylene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione

“…Within the octahydroindolizine fused ring system, the piperidine ring is in a chair conformation and the pyrrole ring is twisted about the N2-C8 bond. The C-C bond lengths and C-C-C angles in the acenaphthylene group compare with those of related structures (Hazell & Hazell, 1977;Hazell & Weigelt, 1976;Jones et al, 1992;Sundar et al, 2002). The observed conformation of the pyrrole ring may be due to the presence of an intramolecular C8 -H8···O2 interaction ( Table 1).…”

“…For related acenaphthylene structures, see: Hazell & Hazell (1977); Hazell & Weigelt (1976); Jones et al (1992); Sundar et al (2002). Table 1 Hydrogen-bond geometry (Å , ).…”

Intermolecular C—H...O and C—H...Xinteractions in substituted spiroacenaphthylene structures

“…The C-C bond lengths and C-C-C angles in the acenaphthylene groups of (I)-(III) compare with those of related structures (Hazell, 1976;Hazell & Hazell, 1977;Hazell & Weigelt, 1976;Jones et al, 1992;Sundar et al, 2002). The C8-N2 bond length is 1.451 (3) Å in (I), 1.448 (3) Å in (II) and 1.455 (3) Å in (III), and these values are comparable with the Csp 2 -Nsp 2 distances found in similar structures (Sussman & Wodak, 1973;Wodak, 1975).…”