Acta Crystallographica Section C

Volume 65, Part 9 (September 2009)

organic compounds

dn3123 scheme

Acta Cryst. (2009). C65, o460-o464 [ doi:10.1107/S0108270109030960 ]

Lamotrigine, an antiepileptic drug, and its chloride and nitrate salts

B. Sridhar and K. Ravikumar

Abstract: In lamotrigine [systematic name: 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine], C₉H₇Cl₂N₅, (I), the asymmetric unit contains one lamotrigine base molecule. In lamotriginium chloride [systematic name: 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium chloride], C₉H₈Cl₂N₅⁺·Cl^-, (II), the asymmetric unit contains one lamotriginium cation and one chloride anion, while in lamotriginium nitrate, C₉H₈Cl₂N₅⁺·NO₃^-, (III), the asymmetric unit contains two crystallographically independent lamotriginium cations and two nitrate anions. In all three structures, N-HN hydrogen bonds form an R₂²(8) dimer. In (I) and (II), hydrophilic layers are sandwiched between hydrophobic layers in the crystal packing. In all three structures, hydrogen bonds lead to the formation of a supramolecular hydrogen-bonded network. The significance of this study lies in its illustration of the differences between the supramolecular aggregation in the lamotrigine base and in its chloride and nitrate salts.

Formula: C₉H₇Cl₂N₅, C₉H₈Cl₂N₅⁺·Cl^- and C₉H₈Cl₂N₅⁺·NO₃^-


	Structure factor file (CIF format) (92.1 kbytes) [ doi:10.1107/S0108270109030960/dn3123Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (104.2 kbytes) [ doi:10.1107/S0108270109030960/dn3123IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (222.4 kbytes) [ doi:10.1107/S0108270109030960/dn3123IIIsup4.hkl ] Contains datablock III

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