The crystal structure of tris(4-aminophenylthio)arsine, As(SC6H4-4-NH2)3

The reaction of a suspension of arsenic(III) oxide in deoxygenated methanol with redistilled 4-aminothiophenol at 25 degrees C for 24 h afforded tris(4-aminophenylthio)arsine. Crystals suitable for X-ray analysis were obtained by recrystallization from chloroform. The compound is monoclinic [P2(1)/n, 11.6427(2) angstrom, 9.3726(2) angstrom, 17.7788(4) angstrom, beta = 99.854(2)degrees, Z = 4]. Its supramolecular organization is based on strong (N-H center dot center dot center dot N, N-H center dot center dot center dot S) and weak (C-H center dot center dot center dot S) intermolecular hydrogen bonding together with C-H center dot center dot center dot pi interactions among the discrete molecular units. The crystal data of this and other As(III) trithiolates are compared and discussed in the light of probable operation of the alpha-effect in their nucleophilic reactions.