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Reaction of the lithium salt of 1-(2'-pyridyl)-ortho-carborane, Li[1-R-1,2-C(2)B(10)H(10)](R = 2'-NC(5)H(4)), with sulfur, followed by hydrolysis, gave the mercapto-o-carborane, 1-R-2-SH-1,2-C(2)B(10)H(10) which forms chiral crystals containing helical chains of molecules linked by intermolecular S-H...N hydrogen bonds. The cage C(1)-C(2) and exo C(2)-S bond lengths (1.730(3) and 1.775(2)[Angstrom], respectively) are indicative of exo S=C pi bonding. The tin derivative 1-R-2-SnMe(3)-1,2-C(2)B(10)H(10), prepared from Li[1-R-1,2-C(2)B(10)H(10)] and Me(3)SnCl, crystallises with no significant intermolecular interactions. The pyridyl group lies in the C(1)-C(2)-Sn plane, oriented to minimise the NSn distance (2.861(3)[Angstrom]). The tin environment is distorted trigonal bipyramidal with axial N and Me. The gold derivative 1-R-2-AuPPh(3)-1,2-C(2)B(10)H(10), prepared from Li[1-R-1,2-C(2)B(10)H(10)] and AuCl(PPh(3)), reveals no NAu interaction in its crystal structure.

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Sulfur, tin and gold derivatives of 1-(2′-pyridyl)-ortho-carborane, 1-R-2-X-1,2-C2B10H10(R = 2′-pyridyl, X = SH, SnMe3or AuPPh3)