Abstract
In the title compound, C11H12N4O5, the mean plane through the nitro substituent on the benzene ring is inclined to the benzene mean plane by 85.8 (2)°, which avoids steric interactions with the ortho substituents. The hydroxy group is involved in bifurcated hydrogen bonds. The first is an intramolecular O—H⋯O hydrogen bond, involving the ester carbonyl O atom, which gives rise to the formation of a boat-like hydrogen-bonded chelate ring. The second is an intermolecular O—H⋯N hydrogen bond involving the first N atom of the azide group of a symmetry-related molecule. In the crystal structure this leads to the formation of a polmer chain extending in the c-axis direction.
Highlights
C11H12N4O5, the mean plane through the nitro substituent on the benzene ring is inclined to the benzene mean plane by 85.8 (2), which avoids steric interactions with the ortho substituents
The hydroxy group is involved in bifurcated hydrogen bonds
Related literature For literature related to the antitumor properties of rhazinilam, see: Bonneau et al (2007)
Summary
The hydroxy group is involved in bifurcated hydrogen bonds. The first is an intramolecular O—HÁ Á ÁO hydrogen bond, involving the ester carbonyl O atom, which gives rise to the formation of a boatlike hydrogen-bonded chelate ring. The second is an intermolecular O—HÁ Á ÁN hydrogen bond involving the first N atom of the azide group of a symmetry-related molecule. For literature related to the synthesis and structure–activity relationships of rhazinilam analogues, see: Decor et al (2006); Baudoin et al (2002); Ghosez et al (2001); Rubio & Bornmann (2001); Dupont et al (2000, 1999); Alazard et al (1996). For literature related to the synthesis of pyrrolinone precursors, see: Vallat (2004); Vallat et al (2009)
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