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

Grossie D, Harrison L, Turnbull K - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The carbonyl side chain is twisted relative to the syndone ring by 15.8 (2)°.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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Wright State University, Chemistry, 3649 Colonel Glenn Hwy, Dayton, Ohio 45435, USA.

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-1,2,3λ(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 π-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.

No MeSH data available.


Related in: MedlinePlus

The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4257336&req=5

Fap1: The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.


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

Grossie D, Harrison L, Turnbull K - Acta Crystallogr Sect E Struct Rep Online (2014)

The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257336&req=5

Fap1: The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
Bottom Line: The carbonyl side chain is twisted relative to the syndone ring by 15.8 (2)°.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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Wright State University, Chemistry, 3649 Colonel Glenn Hwy, Dayton, Ohio 45435, USA.

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-1,2,3λ(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 π-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.

No MeSH data available.


Related in: MedlinePlus