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, orI andII, respectively) crystallize in the orthorhombic space groupP2₁2₁2₁ (No. 19, D ₂ ⁴ ) with four formula units per cell anda=5.209(1),b=17.501(1),c=20.154(1)Å anda=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 toR=0.046 and 0.052. In both structures, the toluenesulfonamide group occupies a positionanti 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 thetrans isomerI having both groups equatorial, while thecis isomerII 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.(2S,5R)- and (2R,5R)-4-Methylbenzenesulfonic acid-5-methyl-2-(1-methylethyl)cyclohexylidene]hydrazide.