Synthesis, characterization, and X-ray crystal structure of di-(2,4-imidazolidinedione-5-ethyl)disulfide, C10H14N4O4S2

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Di-(2,4-imidazolidinedione-5-ethyl)disulfide or homocystine hydantoin, C10H14N4O4S2 (I), crystallizes in the non-centrosymmetric space group P21 (No. 4) with two molecules in the unit cell with a = 7.132(1), b = 9.282(2), c = 10.770(2) Å and β = 105.68(1)°. The two imidazolidinedione rings are planar with a dihedral angle of 46.9°. The rings are joined by a diethyl disulfide bridge at chiral centers on the rings. The C– S– S– C torsion angle is −80°(−sc). The absolute stereochemistry of the chiral centers was determined to be (5S, 5′S), η = + 0.92 (11). Important bond distances include: S– S = 2.022(4); S– C (mean) = 1.809(8); and C= O (mean) = 1.224(7) Å. The compound is stabilized by a network of intermolecular carbonyl-to-amine hydrogen bonding and van der Waals cohesive forces.

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