Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 10 (October 2013)

organic compounds

lg3120 scheme

Acta Cryst. (2013). C69, 1164-1169    [ doi:10.1107/S0108270113023573 ]

Solvent-mediated pseudo-quadruple hydrogen-bond motifs in three lamotrigine-carboxylic acid complexes

B. Sridhar, J. B. Nanubolu and K. Ravikumar

Abstract: Lamotrigine, an antiepileptic drug, has been complexed with three aromatic carboxylic acids. All three compounds crystallize with the inclusion of N,N-dimethylformamide (DMF) solvent, viz. lamotriginium [3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium] 4-iodobenzoate N,N-dimethylformamide monosolvate, C9H8Cl2N5+·C7H4IO2-·C3H7NO, (I), lamotriginium 4-methylbenzoate N,N-dimethylformamide monosolvate, C9H7Cl2N5+·C8H8O2-·C3H7NO, (II), and lamotriginium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate, C9H8Cl2N5+·C7H3N2O7-·C3H7NO, (III). In all three structures, proton transfer takes place from the acid to the lamotrigine molecule. However, in (I) and (II), the acidic H atom is disordered over two sites and there is only partial transfer of the H atom from O to N. In (III), the corresponding H atom is ordered and complete proton transfer has occurred. Lamotrigine-lamotrigine, lamotrigine-acid and lamotrigine-solvent interactions are observed in all three structures and they thereby exhibit isostructurality. The DMF solvent extends the lamotrigine-lamotrigine dimers into a pseudo-quadruple hydrogen-bonding motif.

Formula: C9H7.54Cl2N5+·C7H4.46IO2-·C3H7NO, C9H7Cl2N5+·C8H8O2-·C3H7NO and C9H8Cl2N5+·C7H3N2O7-·C3H7NO

Keywords: crystal structure; solvated lamotrigine salts; hydrogen bonding; anticonvulsants; antiepilepsy drugs; active pharmaceutical ingredients; isostructurality.

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Chemical Markup Language (CML) file (7.9 kbytes)
[ doi:10.1107/S0108270113023573/lg3120Isup5.cml ]
Supplementary material

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Chemical Markup Language (CML) file (8.2 kbytes)
[ doi:10.1107/S0108270113023573/lg3120IIsup6.cml ]
Supplementary material

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[ doi:10.1107/S0108270113023573/lg3120IIIsup7.cml ]
Supplementary material


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