3-(2-Acetamido-phen-yl)sydnone

Abstract

Sydnones are unusual mesoionic compounds containing a five-membered heterocyclic ring. Generally for stability, substitution at the N-3 position by an aromatic fragment is necessary. In the title compound, C(10)H(9)N(3)O(3), the aromatic substitutent is 2-acetamido-phenyl. The two planar ring fragments are twisted relative to one another, with a inter-planar angle of 63.13 (5)°. The mol-ecules are packed into the unit cell via π-π inter-actions between the phenyl rings [inter-planar separation = 3.4182 (4) Å] and between the sydnone rings [inter-planar separation = 3.2095 (4) Å]. N-H⋯O and C-H⋯O hydrogen bonding is also found inter-nally and externally to the mol-ecule.

Fig. 1.

Molecular structure of title compound with the atom numbering scheme. The displacement ellipsoids are drawn at 50% probability level. The H atoms are presented as a small spheres of arbitrary radius.