Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 12 (December 2013)

organic compounds

Acta Cryst. (2013). C69, 1516-1523    [ doi:10.1107/S0108270113028965 ]

Tosyl­ate salts of the anti­cancer drug lapatinib

K. Ravikumar, B. Sridhar, J. B. Nanubolu, A. K. S. B. Rao and R. Jyothiprasad

Abstract: Two tosyl­ate salts of an anti­cancer drug lapatinib, viz. a mono­tosyl­ate [systematic name: ({5-[4-({3-chloro-4-[(3-fluoro­phen­yl)meth­oxy]phen­yl}amino)­quinazolin-6-yl]furan-2-yl}meth­yl)[2-(methyl­sulfon­yl)eth­yl]aza­nium 4-methyl­benzene­sulfonate], C29H27ClFN4O4S+·C7H7O3S-, (I), and a di­tosyl­ate [systematic name: 4-({3-chloro-4-[(3-fluoro­phen­yl)meth­oxy]phen­yl}amino)-6-]5-({[2-(methyl­sulfon­yl)eth­yl]aza­nium­yl}meth­yl)furan-2-yl[quinazolin-1-ium bis­(4-methyl­benzene­sulfonate)], C29H28ClFN4O4S2+·2C7H7O3S-, (II), were ob­tained during crystallization attempts for polymorphism. In both structures, the lapatinib cation is in a distorted U-like conformation and the tosyl­ate anion is clamped between the aniline N atom and methyl­amine N atom through N-H...O hydrogen bonds, forming an R22(15) ring motif. The 4-ani­­lino­quinazoline ring system is essentially planar in (I), while it is twisted in (II), controlled by an intra­molecular C-H...N inter­action. In (I), alternating cations and anions are linked by N-H...O hydrogen bonds into C22(6) chains. These chains are linked by cations in a helical manner. The presence of the additional tosyl­ate anion in (II) results in the formation of one-dimensional tapes of fused hydrogen-bonded rings through N-H...O and C-H...O inter­actions. These studies augment our understanding of the role of nonbonded inter­actions in the solid state, which is useful for correlation to the physicochemical properties of drug products.

CCDC references: 967691 and 967692

Formula: C29H27ClFN4O4S+·C7H7O3S- and C29H28ClFN4O4S2+·2C7H7O3S-

Keywords: crystal structure; lapatinib; anti­cancer drug; tosyl­ate salts; pharmaceuticals; hydrogen bonding.

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[ doi:10.1107/S0108270113028965/ov3039Isup4.cml ]
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