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. 2018 Apr 19;74(Pt 5):678-681.
doi: 10.1107/S2056989018005819. eCollection 2018 May 1.

Lamotrigine ethanol monosolvate

Charlie L Hall  1 , Jason Potticary  1 , Hazel A Sparkes  1 , Natalie E Pridmore  1 , Simon R Hall  1
Affiliations

Lamotrigine ethanol monosolvate

Charlie L Hall et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

Lamotrigine is an active pharmaceutical ingredient used as a treatment for epilepsy and psychiatric disorders. Single crystals of an ethano-late solvate, C9H7Cl2N5·C2H5OH, were produced by slow evaporation of a saturated solution from anhydrous ethanol. Within the crystal structure, the lamotrigine mol-ecules form dimers through N-H⋯N hydrogen bonds involving the amine N atoms in the ortho position of the triazine group. These dimers are linked into a tape motif through hydrogen bonds involving the amine N atoms in the para position. The ethanol and lamotrigine are present in a 1:1 ratio in the lattice with the ethyl group of the ethanol mol-ecule exhibiting disorder with an occupancy ratio of 0.516 (14):0.484 (14).

Keywords: crystal structure; ethano­late; lamotrigine.

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Figures

Figure 1
Figure 1
A displacement ellipsoid plot of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Figure 2
The crystal packing of (I), viewed along the c axis.
Figure 3
Figure 3
The bonding motif of adjacent lamotrigine dimers. The angle between the dimers was calculated using the planes of the indicated triazine rings.
Figure 4
Figure 4
(a) The dimerization motif in (I), held together with the amines in the ortho position of the triazine group. The amine in the ortho and para positions are labelled with O and P, respectively. (b) The dimerization motif in the ethano­late hydrate structure, held together with the amines in the para position of the triazine group.
See this image and copyright information in PMC

References

    1. Bruker (2015). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin USA.
    1. Cheney, M. L., Shan, N., Healey, E. R., Hanna, M., Wojtas, L., Zaworotko, M. J., Sava, V., Song, S. & Sanchez-Ramos, J. R. (2010). Cryst. Growth Des. 10, 394–405.
    1. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
    1. Garti, N., Berkovich, Y., Dolitzky, B. Z., Aronhime, J., Singer, C., Liebermann, A. & Gershon, N. (2008). US Patent Number. 7390807B2.
    1. Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. - PMC - PubMed

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