Crystal structures of 3-methyl-1,2,4-benzotriazine 1-oxide and 2-oxide

The compound 3-methyl 1,2,4-benzotriazine 1,4-dioxide (1) belongs to a new class of clinically promising, bioreductively-activated antitumor drugs. Reductive metabolism of these triazine di-N-oxides typically produces mixtures of mono-N-oxide analogues. As part of our efforts toward characterization of the in vitro metabolism of 1, we synthesized the 1-oxide (2) and 2-oxide (3) analogues and characterized these compounds using X-ray crystallography. Compounds 2 and 3 (C₈H₇N₃O) crystallized in the monoclinic space group P2₁/c. Unit cell parameters for 2: a = 9.0466(7), b = 10.5959(8), c = 7.8981(6) ?, β = 98.4940(10), and z = 4. Unit cell parameters for 3: a = 5.7193(4), b = 9.3774(7), c = 13.8427(11) ?, β = 101.6370(10), and z = 4.Supplementary material X-ray crystallographic data reported in this paper is deposited with the Cambridge Crystallographic Data Center as supplementary publication numbers CCDC 294738 (compound 2) and CCDC 294739 (compound 3). Copies of available material can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK.