Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 8 (August 2009)

organic compounds

 

Structures of 1-hydrophenanthroimidazoles: building blocks in the synthesis of expanded-ring bis(imidazoles)

R. T. Stibrany and J. A. Potenza

Abstract: The structures of 1H-phenanthro[9,10-d]imidazole, C₁₅H₁₀N₂, (I), and 3,6-dibromo-1H-phenanthro[9,10-d]imidazole hemihydrate, C₁₅H₈Br₂N₂·0.5H₂O, (II), contain hydrogen-bonded polymeric chains linked by columns of - stacked essentially planar phenanthroimidazole monomers. In the structure of (I), the asymmetric unit consists of two independent molecules, denoted (Ia) and (Ib), of 1H-phenanthro[9,10-d]imidazole. Alternating molecules of (Ia) and (Ib), canted by 79.07 (3)°, form hydrogen-bonded zigzag polymer chains along the a-cell direction. The chains are linked by - stacking of molecules of (Ia) and (Ib) along the b-cell direction. In the structure of (II), the asymmetric unit consists of two independent molecules of 3,6-dibromo-1H-phenanthro[9,10-d]imidazole, denoted (IIa) and (IIb), along with a molecule of water. Alternating molecules of (IIa), (IIb) and water form hydrogen-bonded polymer chains along the [110] direction. The donor-acceptor distances in these N(imine)H-O(water)H-N(amine) hydrogen bonds are the shortest thus far reported for imidazole amine and imine hydrogen-bond interactions with water. Centrosymmetrically related molecules of (IIa) and (IIb) alternate in columns along the a-cell direction and are canted by 48.27 (3)°. The present study provides the first examples of structurally characterized 1H-phenanthroimidazoles.

Formula: C₁₅H₁₀N₂ and C₁₅H₈Br₂N₂·0.5H₂O

	Structure factor file (CIF format) (103.0 kbytes) [ doi:10.1107/S0108270109025165/fg3095Isup2.hkl ] Contains datablock I
	Structure factor file (CIF format) (261.0 kbytes) [ doi:10.1107/S0108270109025165/fg3095IIsup3.hkl ] Contains datablock II

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