Methyl (3R*,3′S*)-1′,1′′-dimethyl-2,2′′-dioxodispiro[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxylate

Abstract

In the title compound, C22H21N3O4, the central pyrrolidine ring adopts an envelope conformation with the N atom in the flap position. The indoline ring systems are almost perpendic­ular to the mean plane of the pyrrolidine ring, making dihedral angles of 86.4 (8) and 83.1 (8)°. The acetate group attached to the pyrrolidine ring assumes an extended conformation. In thecrystal, N—H⋯O hydrogen bonds result in the formation of a C(7) chain running along [100]. The crystal packing also features π–π inter­actions [centroid–centroid distance = 3.2032 (11) Å].

4′-Methyl-1H-14′,19′-dioxa-4′-azaspiro[indole-3,5′-tetracyclo[18.4.0.02,6.08,13]tetracosane]-1′(24′),8′,10′,12′,20′,22′-hexaene-2,7′(3H)-dione

“…The bond lengths and angles in the title molecule ( Fig. 1) are within normal ranges and comparable to those found in a related structure (Ganesh et al, 2012). The indoline ring system (C4-C11/N2) is essentially planar, with maximum deviation of 0.027 (2) Å for atom C5; O2 lies 0.102 (1) Å out of the leastsquares plane of the indole ring.…”

“…For background to natural and synthetic pharmacologically active pyrrolidines, see: Waldmann (1995). For related structures, see: Ganesh et al (2012); Narayanan et al (2012). For graph-set notation, see: Bernstein et al (1995).…”

A triclinic polymorph of methyl (3R,3′S)-1′,1′′-dimethyl-2,2′′-dioxodispiro[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxylate

“…The crystal packing is further consolidated by strong interactions with a centroid-centroid distance of 3.2585 (8) Å . The title compound is a polymorph of previously reported monoclinic structure [Ganesh et al (2012). Acta Cryst.…”

“…We have recently reported the structure of the title compound in the monoclinic system (Ganesh et al, 2012). Here we report the structural details of its triclinic polymorph.…”

Crystal structure of ethyl 1′,5-dimethyl-2′′,3-dioxo-3H-dispiro[benzo[b]thiophene-2,3′-pyrrolidine-2′,3′′-indoline]-4′-carboxylate

“…For details of highly functionalized pyrrolidines as the main structural element of many natural and synthetic pharmacologically active compounds, see: Waldmann (1995). For the crystal structure of a related compound, see: Ganesh et al (2012)…”