Crystal structure of 4-(2-bromo-prop-ion-yl)-3-phenyl-sydnone.

ABSTRACT: Sydnones are a class of mesoionic compounds containing a five-membered heterocyclic ring. In general, sydnone com-pounds are synthesized with an aromatic substutuent at the N(3) position. This feature, adds to the stability of the heterocyclic ring. In the title compound {systematic name: 4-(2-bromo-propano-yl)-3-phenyl-1,2,3?(5)-oxa-diazol-3-ylium-5-olate}, C11H9BrN2O3, the aromatic substitutent is an unsubstituted phenyl ring. The sydnone ring is almost planar, with a maximum deviation from the mean plane of 0.023?(1)?Å, but is not coplanar with the phenyl ring, having a dihedral angle of 40.93?(8)°. The carbonyl side chain is twisted relative to the syndone ring by 15.8?(2)°. The mol-ecules are packed in the unit cell as pairs related by an inversion center at (1, 0, 1/2). The pairs inter-act via ?-stacking, with the distance separating the centroids being 3.824?(1)?Å. The Br atom has two contacts, one to an N atom in a neighboring asymmetric unit with a distance of 3.346?(2)?Å (the sum of the van der Waals radii is 3.40?Å) and a second to an H atom with a distance of 3.03?Å. The contact with the H atom is perpendicular (C-Br?H = 98.60°) to the C-Br bond, and that to the N atom is linear [C-Br?N = 169.10?(5)°] to the C-Br bond. The O atom of the sydnone ring is involved in two hydrogen bonds, one intra-molecular with a donor-acceptor distance of 3.1486?(19)?Å and a second that is inter-molecular, with a phenyl H atom as the donor and has a donor-acceptor distance of 3.346?(2)?Å.

SUBMITTER: Grossie D 

PROVIDER: S-EPMC4257336 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature