Structure analyses of menthone- and isomenthone-tosylhydrazones, C17H26N2O2S


The crystal and molecular structures of two configurational isomers of the title compound have been determined by three-dimensional, single-crystal X-ray diffractometry. Both (2S,5R)- and (2R,5R)-4-methylbenzenesulfonic acid-[5-methyl-2-(1-methylethyl)cyclohexylidene] hydrazide (hereafter referred to as menthone- and isomenthone-tosylhydrazone, or I and II, respectively) crystallize in the orthorhombic space group P212121 (No. 19, D24) with four formula units per cell and a=5.209(1), b=17.501(1), c=20.154(1)Å and a=5.281(1), b=17.300(1), c=20.422(1)Å, respectively. The phase problems were solved by direct methods and the respective final full-matrix least-squares refinements of 1767 and 3010 unique reflections converged to R=0.046 and 0.052. In both structures, the toluenesulfonamide group occupies a position anti to the more substituted side of the cyclohexyl ring, the C(16)-C(11)-N(2) angles are significantly wider than 120°, and each sulfonamide nitrogen (1) atom appears to exhibit a distorted trigonal pyramidal geometry. The structures differ in the positioning of the isopropyl and methyl substituents on the cyclohexane ring, with the trans isomer I having both groups equatorial, while the cis isomer II exhibits an axial isopropyl group. The molecules in the crystal lattice are held together by van der Waals forces. X-ray powder diffraction, conoscopic, infrared, and1H and13C NMR analyses have been performed. © 1992 Plenum Publishing Corporation.

Publication Title

Journal of Crystallographic and Spectroscopic Research