Structure of a novel, macrocyclic Schiff base

(E,E)-1,2,3,4,4a alpha, 12a beta-Hexahydro-7,7,10,- 10-tetramethyl-7H,10H-8,9-dithia-5,12-diazabenzo-cyclodec ene, C14H24N2S2, Mr = 284.49, monoclinic, P2(1)/n, a = 8.962 (1), b = 19.356 (3), c = 10.178 (1) A, beta = 114.49 (1) degrees, V = 1606.7 (7) A3, Z = 4, Dm = 1.21 (1), D chi = 1.176 Mg m-3, mu (Mo K alpha, lambda = 0.71073 A) = 0.31 mm-1, F(000) = 616, T = 296 (1) K, RF = 0.031 for 2066 reflections. The molecule has approximate point symmetry 2 and consists of a 1,2-trans-disubstituted cyclohexane (chair conformation) fused to a ten-membered ring that contains one disulfide and two, trans-substituted, imino groups. Structural parameters associated with the disulfide group, including the C-S-S-C torsion angle [90.8 (1) degrees], are similar to those reported for several acyclic disulfides. The N-C-C-N torsion angle [-63.1 (2) degrees] associated with disubstitution of the cyclohexane ring is substantially larger than those found for protonated or chelated 1,2-trans-diamino-cyclohexane.