Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 12 (December 2005)

organic compounds

ln1187 scheme

Acta Cryst. (2005). C61, o707-o710 [doi:10.1107/S0108270105035651]

The methanol disolvate and the dihydrate of fexofenadine, an antihistamine drug

L. Tessler and I. Goldberg

Abstract: Fexofenadine [systematic name: (±)-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidinium-1-yl]-butyl}phenyl)-2-methylpropionate], crystallizes in two forms, viz. as the methanol disolvate, C₃₂H₃₉NO₄·2CH₄O, and as the dihydrate, C₃₂H₃₉NO₄·2H₂O. It exists in the two structures as a zwitterion, which self-assembles as dimers sustained by a pair of charged-assisted N-HOOC hydrogen bonds. In the methanol disolvate, the supramolecular organization consists of discrete fexofenadine dimers solvated by four molecules of methanol. The dihydrate structure is sustained by a more extended hydrogen-bonding scheme, wherein the hydrated dimeric entities are interlinked by additional hydrogen bonds. The fexofenadine molecule adopts different and differently disordered conformations of the 1-hydroxybutyl residue in the two structures.

Formula: C₃₂H₃₉NO₄·2CH₄O and C₃₂H₃₉NO₄·2H₂O


	Structure factor file (CIF format) (358.0 kbytes) Contains datablock I

	Structure factor file (CIF format) (342.4 kbytes) Contains datablock II

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