4′-Methyl-1H-14′,19′-dioxa-4′-azaspiro[indole-3,5′-tetracyclo[18.4.0.0^2,6.0^8,13]tetracosane]-1′(24′),8′,10′,12′,20′,22′-hexaene-2,7′(3H)-dione

Abstract

In the title compound, C29H28N2O4, the indoline ring system is essentially planar, with a maximum deviation of 0.027 (2) Å; the carbonyl O atom lies 0.102 (1) Å out of the least-squares plane of the indole ring. The pyrrolidine ring adopts a C-envelope conformation, with a C atom displaced by 0.643 (2) Å from the mean plane formed by the remaining ring atoms. The pyrrolidine ring makes a dihedral angle of 86.1 (8)° with the indoline ring system. In the crystal, N—H⋯O hydrogen bonds result in the formation of cyclic centrosymmetric dimers [R 2 2(8)]. C—H⋯π inter­actions also occur, leading to a chain along the b-axis direction. There is a rather weak π–π electron inter­action between the pyrrazole and benzene rings, with a centroid–centroid distance of 3.765 (1) Å.

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

“…The bond lengths and angles in the title molecule ( Fig. 1) are within normal ranges and comparable to those found in closely related structures (Narayanan et al, 2012;Augustine et al, 2010). The acenaphthylene ring system (C4-C15) is essentially planar (rmsd 0.0290 Å).…”

“…Highly functionalized pyrrolidines have gained much interest in the past few years as they constitute the main structural element of many natural and synthetic pharmacologically active compounds (Waldmann, 1995). In continuation of our work on the crystal structure analysis of spiro-pyrrolidine derivatives (Narayanan et al, 2012), the crystal structure of the title compound has been carried out and the results are presented here.…”

“…For background to natural and synthetic pharmacologically active pyrrolidines, see: Waldmann (1995). For related structures, see: Augustine et al (2010); Narayanan et al (2012). For graph-set motifs, see: Bernstein et al (1995).…”