(Z)-5-(2-thienylmethylene)-2,4-imidazolidinedione.
The major product formed in the thermolysis of 5-diazouracil in thiophene at 423-433 K has been identified as the unexpected compound (Z)-5-(2-thienylmethylene)-2,4-imidazolidinedione, C8H6N2O2S, by X-ray analysis. The molecule is a hydantoin derivative with a thienylmethylene group substituted at the 5-position. The structure is disordered in that the thiophene ring exists in two orientations which are related by an approximate 180 degree rotation about the C(6)-C(7) bond. All of the N and O atoms are involved in an intermolecular hydrogen-bonding network via N-H...O interactions. This network consists of an infinite chain along the a-axis direction and a cyclic trimer arrangement which branches from this chain. The molecules are arranged in the unit cell in pleated sheets which are approximately perpendicular to the c axis.
Gallucci
J C
JC
Department of Chemistry, Ohio State University, Columbus 43210, USA.
Mathur
N
N
Shechter
H
H
D018360:Crystallography, X-Ray; D006358:Hot Temperature; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D048289:Imidazolidines; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013876:Thiophenes / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
C094405:5-(2-thienylmethylene)-2,4-imidazolidinedione; D007093:Imidazoles; D048289:Imidazolidines; D013876:Thiophenes; C004758:5-diazouracil; D014498:Uracil