Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 3 (March 2014)


metal-organic compounds



gz3246 scheme

Acta Cryst. (2014). C70, 260-266    [ doi:10.1107/S2053229614001843 ]

In-house and synchrotron X-ray diffraction studies of 2-phenyl-1,10-phenanthroline, protonated salts, com­plexes with gold(III) and copper(II), and an orthometallation product with palladium(II)

J. A. Krause, D. Zhao, S. Chatterjee, R. Falcon, K. Stoltz, J. C. Warren, S. E. Wiswell, W. B. Connick and S. N. Collins

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-[kappa]N10)gold(III), [AuCl3(C18H12N2)], (VI). Di­chlorido­(2-phenyl-1,10-phenanthroline-[kappa]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-[kappa]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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Structure factor file (CIF format) (232.2 kbytes)
[ doi:10.1107/S2053229614001843/gz3246Isup2.hkl ]
Contains datablock I


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Structure factor file (CIF format) (162.6 kbytes)
[ doi:10.1107/S2053229614001843/gz3246IIsup3.hkl ]
Contains datablock II


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Structure factor file (CIF format) (146.0 kbytes)
[ doi:10.1107/S2053229614001843/gz3246IIIsup4.hkl ]
Contains datablock III


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Structure factor file (CIF format) (160.0 kbytes)
[ doi:10.1107/S2053229614001843/gz3246IVsup5.hkl ]
Contains datablock IV


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Structure factor file (CIF format) (138.8 kbytes)
[ doi:10.1107/S2053229614001843/gz3246Vsup6.hkl ]
Contains datablock V


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Structure factor file (CIF format) (144.8 kbytes)
[ doi:10.1107/S2053229614001843/gz3246VIsup7.hkl ]
Contains datablock VI


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Structure factor file (CIF format) (135.3 kbytes)
[ doi:10.1107/S2053229614001843/gz3246VIIsup8.hkl ]
Contains datablock VII


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Structure factor file (CIF format) (212.1 kbytes)
[ doi:10.1107/S2053229614001843/gz3246VIIIsup9.hkl ]
Contains datablock VIII


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