The ribonucleotide reductase R1 inhibitor N-acetyl-N,Ο-di(propylcarbamoyl)hydroxylamine, an analogue of caracemide

The molecular structure of the caracemide analogue N-acetyl-N,Ο-di(propylcarbamoyl)hydroxylamine (Chemical Abstracts nomenclature: N-[(propylamino)carbonyl]-N-{[(propylamino)carbonyl]oxy}acetamide), C₁₀H₁₉N₃O₄, is comparable to the structure of the parent compound N-acetyl-N,Ο-di(methylcarbamoyl)hydroxylamine. The caracemide moiety of the compound consists of two nearly planar moieties, which are almost perpendicular to each other as in the crystal structure of caracemide itself. The two propyl groups in each of the two molecules (A and B) in the asymmetric unit have different conformations. One of these groups adopts the gauche conformation, with torsion angles of 49.1 (6) and -61.3(4)° for molecules A and B, respectively, while the other adopts a fully extended conformation, with respective torsion angles of 179.2 (3) and 176.5 (3)°. The main differences in bond lengths, angles and torsion angles between molecules A and B are found in one of the propyl groups.