Crystal structures of two new monoprotonated products of 1,4,7-trimethyl-1,4,7-triazacyclononane: (Me-3[9]aneN(3)H) (SO3CF3) and (Me-3[9]aneN(3)H)I

Two new monoprotonated products of macrocyclic polyamine 1, 4, 7-trimethyl- 1, 4, 7-triazacyclononane(Me-3(9)aneN(3)), (Me-3(9)aneN(3)H)(SO3CF3) 1 (C-1 0 H22N3O3SF3, M-r = 321. 36) and (Me-3(9)aneN(3)H)I 2 (C9H22N3I, M-r = 299. 20) were obtained by the reactions of Me-3(9)aneN(3) and yttrium triflate or ytterbium diiodide as the unexpected products. The crystal structures of compounds 1 and 2 have been determined. Crystal 1 is orthorhombic, space g roup P2(1)2(1)2(1)(#19), a = 12. 609(3), b = 13. 531(1), c = 9. 225(3) Angs trom, V = 1573. 9(7) Angstrom (3), Z = 4, D-c = 1. 356 g/cm(3), mu = 2. 47 cm(-1), F(000) = 680 and R = 0. 052, R-w = 0. 052 for 807 unique reflection s with I > 2 sigma (I). Crystal 2 belongs to the orthorhombic system with s pace group P2(1)2(1)2(1)(#19), a 11. 417(2), b = 13. 099(3), c = 8. 762(2) Angstrom, V=1310. 5(4) Angstrom (3), Z = 4, D-c = 1. 516 g/cm(3), mu = 24. 14 cm(-1), F(000) = 600 and R = 0. 035, R-w = 0. 042 for 1427 unique reflec tions with I>3 sigma(I). The two structures contain the same cyclic framewo rk in which the acid proton is bonded to an amine nitrogen. This proton exh ibits strong intramolecular hydrogen bonds with the other two nitrogen atom s. The methyl groups are directed away from the ring cavity. The bond dista nce between acid proton and an amine nitrogen in compound 2 is extremely sh ort. The bond angles for 1 and 2 also exhibit obvious diversity inside of t riazacyclononae.