Acta Cryst. (2014). C70, 260-266 [ doi:10.1107/S2053229614001843 ]
Abstract: Different salts of the 2-phenyl-1,10-phenanthrolin-1-ium cation, (pnpH)+, are obtained by reacting 2-phenyl-1,10-phenanthroline (pnp), C18H12N2, (I), with a variety of anions, such as hexafluoridophosphate, C18H13N2+·PF6-, (II), trifluoromethanesulfonate, C18H13N2+·CF3SO3-, (III), tetrachloridoaurate, (C18H13N2)[AuCl4], (IV), and bromide (as the dihydrate), C18H13N2+·Br-·2H2O, (V). Compound (I) crystallizes with Z' = 2, with both independent molecules adopting a coplanar conformation. In (II)-(IV), a hydrogen bond exists between the cation and anion, while one of the lattice water molecules serves as a hydrogen-bonded bridge between the cation and anion in (V). Reaction of (I) with HAuCl4 gives the salt complex (IV); however, reaction with KAuCl4 produces the monodentate complex trichlorido(2-phenyl-1,10-phenanthroline-N10)gold(III), [AuCl3(C18H12N2)], (VI). Dichlorido(2-phenyl-1,10-phenanthroline-2N,N')copper(II), [CuCl2(C18H12N2)], (VII), results from the reaction of CuCl2·2H2O and (I), in which the CuII center adopts a tetrahedrally distorted square-planar geometry. The pendent phenyl ring twists to a bisecting position relative to the phenanthroline plane. The square-planar PdII complex, bromido[2-(phenanthrolin-2-yl)phenyl-3C1,N,N']palladium(II), [PdBr(C18H11N2)], (VIII), is obtained from the reaction of (I) with [PdCl2(cycloocta-1,5-diene)], followed by addition of bromine. A coplanar geometry for the pendent ring is adopted as a result of the tridentate bonding motif.
CCDC references: 983576, 983577, 983578, 941963, 983579, 941962, 983580 and 983581
Formula: C18H12N2 and six salts and complexes
Keywords: crystal structure; synchrotron diffraction; protonated salts; 2-phenyl-1,10-phenanthroline; ortho-palladation; hydrogen bonding; multidentate coordination.
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