Nisar, MadihaHaynes, Richard K.Sung, Herman H.-Y.Puschmann, HorstLakerveld, Richard2018-10-112018-10-112018Nisar, M. et al. 2018. 11-Azaartemisinin cocrystals with preserved lactam : acid heterosynthons. CrystEngComm, 20:1205-1219. [http://dx.doi.org/10.1039/C7CE01875D]1466-8033 (Online)http://hdl.handle.net/10394/31354http://dx.doi.org/10.1039/C7CE01875D11-Azaartemisinin (11-Aza) is a potent anti-malarial drug more readily able to form cocrystals than its parent compound. 13 new 1 : 1 and 2 : 1 cocrystal phases from 25 mono- and bi-functional acids are reported here in excellent yield and purity by liquid assisted grinding. X-ray structures of several of these cocrystals reveal R22(8) heterosynthons with short OH–O[double bond, length as m-dash]C H-bonds ≤2.60 Å between the 11-Aza lactam and the coformer acid groups. The new phases can show enhanced aqueous solubility of 11-Aza of 3× after 12 h. Notably diastereospecific cocrystal formation can occur, with the DL-mandelic acid system yielding solely the 11-Azaart : D-mandelic acid 1 : 1 productenArticle