Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 6 (June 2013)

organic compounds

Acta Cryst. (2013). C69, 674-678    [ doi:10.1107/S0108270113012560 ]

Alogliptin and its benzoate salt

T. Gelbrich, V. Kahlenberg and U. J. Griesser

Abstract: The crystal structure of the free base of the anti­diabetic drug alogliptin [systematic name: 2-({6-[(3R)-3-amino­piperidin-1-yl]-3-methyl-2,4-dioxo-1,2,3,4-tetra­hydro­pyrimidin-1-yl}methyl)benzo­nitrile], C18H21N5O2, displays a two-dimensional N-H...O hydrogen-bonded network. It contains two independent mol­ecules, which have the same conformation but differ in their hydrogen-bond connectivity. In the crystal structure of the benzoate salt (systematic name: (3R)-1-{3-[(2-cyano­phenyl)methyl]-1-methyl-2,6-dioxo-1,2,3,6-tetra­hydropyrimidin-4-yl}piperidin-3-aminium benzoate), C18H22N5O2+·C7H5O2-, the NH3+ group of the cation is engaged in three inter­molecular N-H...O hydrogen bonds to yield a hydrogen-bonded layer structure. The benzoate salt and the free base differ fundamentally in the conformations of their alogliptin moieties.

Formula: C18H21N5O2 and C18H22N5O2+·C7H5O2-

hkldisplay filedownload file

Structure factor file (CIF format) (178.1 kbytes)
[ doi:10.1107/S0108270113012560/gz3235Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (195.9 kbytes)
[ doi:10.1107/S0108270113012560/gz3235IIsup3.hkl ]
Contains datablock II


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