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The amido species OHCaneN3(1-formyl-1,4,7-triazacyclononane), [OHCaneN3H]BPh4, (OHC)3aneN3(1,4,7-triformyl-1,4,7-triazacyclononane) and (PhOC)3aneN3(1,4,7-tribenzoyl-1,4,7-triazacyclononane) have been synthesised, characterised and their crystal structures determined. The conformations of these compounds are discussed in terms of their solid-state structures and of their 1H and 13C NMR spectra in solution. Symmetric isomers derived from hindered rotation about the N–C (amide) bond are generally preferred to asymmetric ones, with the N–C(O)R (R = H or Ph) forming a planar unit exo to the triazamacrocycle. Complexation of PdII with OHCaneN3 confirms the bidentate binding of this ligand and affords [Pd(OHCaneN3)2][B(C6F5)4]2·2H2O, the single-crystal structure of which shows the Pd atom at an inversion centre with Pd–N 2.057(13) and 2.065(10)Å. The amide functions lie above and below the square-planar metal centre with Pd N (amide) 3.021(12)Å. The retention of planarity within the amide function upon complexation [torsion angle for C(2)–N(1)–C(10)–O(11)–6(2)°] suggests that there is no interaction between the amide group and the metal centre.
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Journal of the Chemical Society, Dalton Transactions
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