A number of nitrogen mustards have shown significant activity in experimental tumors; however, many of them exhibit erratic behavior in clinical tests. The nitrogen mustard 5-[3,3-bis(2-chloroethyl)-l-triazeno]-pyrazole-4-carboxamide was found to undergo a spontaneous ring closure to form the compound 1-(2-chloroethyl)-3-(4-carbamoylpyrazol-3-yl)-A 2-1,2,3-triazolinium chloride, [CION6CaHI2] ÷ CI -, which shows no in vivo activity in experimental tumors. The structure of this ionic compound was determined by single-crystal X-ray diffraction techniques, using 1253 independent counter-collected reflections. A full-matrix least-squares refinement yielded a conventional R value of 0-0497. The space group is Pbca and the cell dimensions are a= 14.151 (5), b= 16-990 (5) and c= 10.344 (10) ~. The observed density of 1.489 g.cm -3 is consistent with 8 molecules per unit cell, de= 1.490 g.cm -3. The molecule contains a positively charged triazolinium ring with the chloride ion almost symmetrically located above the ring. The planes of the pyrazole and triazolinium rings make an angle of 50 ° while the amide group makes an angle of 22 ° with the pyrazole ring. The amide oxygen atom interacts with the triazolinium ring but on the side opposite to the chloride ion. Both pyrazole tautomers are present in the crystal.
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