Crystal structure of 1′-ethylspiro[chroman-4,4′-imidazolidine]-2′,5′-dione: a hydantoine derivative

Abstract

The title compound, C13H13N2O3, a hydantoin derivative, crystallized with two molecules (A and B) in an asymmetric unit. In molecule A, the imidazolidine ring is twisted about the C—N bond involving the spiro C atom, while in molecule B this ring is flat (r.m.s. deviation = 0.010 Å). The pyran rings in both molecules have distorted half-chair conformations. The mean plane of the imidazolidine ring is inclined to the aromatic ring of the chroman unit by 79.71 (11)° in molecule A and 82.83 (12)° in molecule B. In the crystal, pairs of N—H...O hydrogen bonds link the individual molecules to form A–A and B–B inversion dimers. The dimers are linked via N—H...O and C—H...O hydrogen bonds, forming sheets lying parallel to the bc plane, viz. (011). Within the sheets, the A and B molecules are linked by C—H...π interactions.

Keywords

• crystal structure
• hydantoin derivatives
• imidazolidine
• chroman
• spiro
• hydrogen bonding
• C—H...π interactions