Polymorphs and pseudopolymorphs of N,N'-dithiobisphthalimide

Acta Crystallographica. Section B, Structural Science
Dorcas M M FarrellChoudhury M Zakaria

Abstract

N,N'-Dithiobisphthalimide, C(16)H(8)N(2)O(4)S(2) (I), forms a wide range of polymorphs and solvates (pseudopolymorphs). When (I) is crystallized from methanol it yields a solvent-free polymorph (4), in Pna2(1) with Z' = 1, in which the molecules are linked into chains by a single C-H.O hydrogen bond: crystallization from either acetonitrile or dimethylformamide produces a monoclinic polymorph (5), in P2(1)/c with Z' = 2, also solvent-free, in which the molecules are linked into molecular ladders. Nitromethane forms a monosolvate, C(16)H(8)N(2)O(4)S(2).CH(3)NO(2) (6), in P2(1)/c with Z' = 1, in which the solvent molecules are linked to the molecules of (I) not only via a conventional C-H.O hydrogen bond but also via a polarized multicentre interaction involving all three C-H bonds of the solvent molecule. Chlorobenzene forms a precise hemisolvate, C(16)H(8)N(2)O(4)S(2).0.5C(6)H(5)Cl (7), in P1; with Z' = 1, while ethylbenzene forms an approximate hemisolvate 2C(16)H(8)N(2)O(4)S(2).0.913C(6)H(5)C(2)H(5).0.087H(2)O (8), in P2(1)/c with eight molecules of (I) per unit cell. In both solvates the molecules of (I) are linked, in (7) by pi.pi stacking interactions augmented by weak C-H.O hydrogen bonds and in (8) by stronger C-H.O hydr...Continue Reading

Citations

Apr 23, 2014·Journal of Pharmaceutical Sciences·Xiaoying WangYang Lu
Nov 26, 2015·Acta Crystallographica. Section E, Crystallographic Communications·Matthew J HenleyGeorge Barany

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