
%0 Journal Article
%A Lynch, DE 
%A Smith, G 
%A Byriel, KA 
%A Kennard, CHL 
%T Molecular Cocrystals of Carboxylic Acids. XII. Structures of the 1 : 1 Adducts of 4-Nitrobenzoic Acid and 3,5-Dinitrobenzoic Acid With N,N'-Bis(1-methylethyl)-6-methylthio-1,3,5-triazine-2,4-diamine (Prometryn)
%J Australian Journal of Chemistry
%D 1993/06/01
%V 46
%N 6
%P 921-927
%K 
%R https://doi.org/10.1071/CH9930921
%U https://www.publish.csiro.au/paper/CH9930921 
%X Two 1:1 molecular adducts of the s- triazine herbicide prometryn [N,N&#8242;- bis (1-methylethyl)-6-methylthio-1,3,5-triazine-2,4-diamine] with 4-nitrobenzoic acid, [(C7H4NO4)-(C10H20N5S)+.H2O] (1), and with 3,5-dinitrobenzoic acid, [(C7H3N2O6)-(C10H20N5S)+] (2), have been prepared and characterized. The structure of (1) has been determined by X-ray methods and refined to a residual R 0.055 for 2072 observed reflections. Crystals are monoclinic, space group P21/c with Z 4 in a cell of dimensions a 7.191(4), b 28.359(8), c 10.990(6) &#506;, &#946; 104.75(3)&#176;. The carboxylic acid group protonates a nitrogen of the triazine ring and is involved in a cyclic hydrogen-bonding association with this and with a secondary amine of the side chain [N&#8230;O, 2.76, 2.78(1)&#506;], while the second amine is associated with the lattice water [N&#8230;O, 2.90(1)&#506;]. Spectroscopic methods have been used to confirm the similarity of the molecular associations involving the carboxylic acid groups of the aromatic acids and prometryn in both (1) and (2). 
