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Intriguing High Z″ Cocrystals of Emtricitabine

Emtricitabine
(ECB) afforded dimorphic cocrystals (Forms I, II)
of benzoic acid (BA), whereas p-hydroxybenzoic acid
(PHBA) and p-aminobenzoic acid (PABA) resulted in
high Z″ cocrystals. Intriguingly, the Z″ of cocrystals are trends from 2 to 14 based on
the manipulation of functional groups on the para position of BA (where the H atom is replaced with that of OH or
NH2 group). The ECB–PABA cocrystal consists of six
molecules each and two water molecules in the asymmetric unit (Z″=14) with 2D planar sheets representing the rare pharmaceutical cocrystal. The findings suggest that
the increment of H bond donor(s) systematically via a suitable coformer
is in correspondence with attaining high Z″
cocrystals. Further, solid state NMR spectroscopy in conjunction with
single crystal X-ray diffraction is demonstrated as a significant
tool to enhance the understanding of the number of symmetry independent
molecules in the crystalline lattice and provide insights to the mechanistic
pathways of crystallization.