W. Cunico, Maria de Lourdes G. Ferreira, J. Wardell
Nov 9, 2016
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Journal
Journal of Chemical Crystallography
Abstract
The crystal structures of two hemihydrates of (3S,4aS, 8aS)-N-(1,1-dimethyl)decahydro-2-[(2R,3S)-2-hydroxy-3-[[arylsulfonyl]amino]-4-phenylbutyl]-3-isoquinolinecarboxamides [aryl = 4-nitrophenyl: [(1:X = 4-O2N)2·H2O]; and aryl = 4-bromophenyl: [(1:X = 4-Br)2·H2O] are reported. The chiral anhydrous compounds, prepared from (2S,3S)-Boc-phenylalanine epoxide, have been reported to exhibit moderate antimalarial activity in vitro against Plasmodium falciparum. The molecular conformations and major intermolecular interactions of the two hydrates are similar, despite there being two independent, albeit similar, molecules in [(1:X = Br)2·H2O] compared to only one in [(1:X = 4-O2N)2·H2O]. A common feature of both structures is that each water molecule is linked to four molecules of 1 via classical hydrogen bonds to form [[(1:X)4(H2O)] units, (X = 4-O2N or 4-Br). As a consequence of the water molecules in [(1:X = 4-O2N)2·H2O] being in special positions and the slight differences between molecules, A and B, in [(1:X = 4-Br)2·H2O], the former has as a symmetrical struture. Emanating from each water molecule in both structures are four chains of alternating molecules of water and 1: these are linked into three dimensional arrays. Compound [(1:X = 4-O2N)2H2O] crystallizes in the monoclinic space group C2 with a = 21.1431(9), b = 10.4886(6), c = 15.4597(9) Å, b = 111.145(3)°and Z = 4. Compound [(1:X = 4-O2N)2H2O] crystallizes in the monoclinic space group P21 with a = 11.0860(9), b = 28.559(2), c = 11.5220(10) Å, b = 117.585(3)° and Z = 4.Graphical AbstractA feature of both structures is that each water molecule is linked to four molecules of the sulfonamide via classical hydrogen bonds.