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

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

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

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Sridhar, Balasubramanian Nanubolu, Jagadeesh Babu Ravikumar, Krishnan
Description	Country affiliation: India Author Affiliation: Sridhar B ( X-ray Crystallography Division, CSIR - Indian Institute of Chemical Technology, Hyderabad 500 007, India.)
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, C $_{9}H$ $_{8}Cl$ $_{2}N$ $_{5}$ $^{+}·C$ $_{7}H$ $_{4}IO$ $_{2}$ $^{-}·C$ $_{3}H$ $_{7}NO,$ (I), lamotriginium 4-methylbenzoate N, N-dimethylformamide monosolvate, C $_{9}H$ $_{7}Cl$ $_{2}N$ $_{5}$ $^{+}·C$ $_{8}H$ $_{8}O$ $_{2}$ $^{-}·C$ $_{3}H$ $_{7}NO,$ (II), and lamotriginium 3,5-dinitro-2-hydroxybenzoate N, N-dimethylformamide monosolvate, C $_{9}H$ $_{8}Cl$ $_{2}N$ $_{5}$ $^{+}·C$ $_{7}H$ $_{3}N$ $_{2}O$ $_{7}$ $^{-}·C$ $_{3}H$ $_{7}NO,$ (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.
File Format	HTM / HTML
e-ISSN	20532296
Journal	Acta Crystallographica Section C Crystal Structure Communications
Issue Number	Pt 10
Volume Number	69
Language	English
Publisher	IUCr/Wiley
Publisher Date	2013-10-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Discipline Analytical Chemistry Discipline Crystallography Anticonvulsants Chemistry Carboxylic Acids Solvents Triazines Pharmacology Crystallography, X-ray Hydrogen Bonding Molecular Structure Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article

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