JOURNAL ARTICLE

3′-[(1H-Indol-3-yl)carbonyl]-1′-methyl-2-oxo-4′-(thiophen-2-yl)spiro[indoline-3,2′-pyrrolidine]-3′-carbonitrile

S. Antony InglebertYuvaraj ArunK. SethusankarParamasivan T. Perumal

Year: 2013 Journal:   Acta Crystallographica Section E Structure Reports Online Vol: 69 (10)Pages: o1585-o1585   Publisher: International Union of Crystallography

Abstract

In the title compound, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C-C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thio-phene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019 (3) and 0.090 (3) Å, respectively. In the oxindole fused-ring system, the pyrrole ring adopts an envelope conformation with the spiro C atom as the flap. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules, forming inversion dimers with an R (2) 2(8) ring motif. The dimers are linked by further N-H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (100).

Keywords:
Indoline Pyrrolidine Oxindole Dihedral angle Chemistry Ring (chemistry) Indole test Isatin Pyrrole Hydrogen bond Stereochemistry Crystallography Molecule Catalysis Organic chemistry

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Topics

Crystal structures of chemical compounds
Physical Sciences →  Chemistry →  Inorganic Chemistry
Synthesis and biological activity
Physical Sciences →  Chemistry →  Organic Chemistry
Crystallography and molecular interactions
Physical Sciences →  Chemistry →  Physical and Theoretical Chemistry
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