Strong N–H⋯N hydrogen bonds and weak N–H⋯S  C interactions in controlling the structure of the co-crystals of dithiooxamide with nitrogen heterocycles

Packing incentives and a reliable N–H⋯N–pyridine synthon in co-crystallization of bipyridines with two agrochemical actives

“…The N-H•••N-pyridine hydrogen bond was found to be a reliable synthon for co-crystal design with TM and TE. The inherent weakness of the N-H•••S=C hydrogen bond commonly 65 used in the polymorphs and solvates of TM and TE is likely the cause, as was found for a more simple dithiooxamide by Piotrkowska et al 27 An important goal was to see how much the size difference of TM and TE affects the crystallization behavior and packing of the 70 molecules. For the hydrogen bonded co-crystals of TM and TE the size difference of the molecules was found to effect the structures in a subtle manner.…”

Crystal Landscape of Primary Aromatic Thioamides

“…In contrast, the use of thioamides in cocrystallization is rare, even though they possess potent hydrogen-bond donors . A search of the Cambridge Structural Database , revealed just 112 crystal structures containing a primary thioamide, in comparison to 1826 that contain primary amides (Figure ).…”

From chains to ladders in co-crystals with 2,3-thiophene-15-crown-5, 2,3-naphtho-15-crown-5, and bis-(18-crown-6)-stilbene constructed by weak hydrogen bonding

“…Dithiooxamide molecule a via its two transoriented amino-groups, preferably forms a 1 : 1 alternative chain with 15C5, B15C5, sterically hindered [1.5]dibenzo-18C6, and with lariat ethers, N,N 0 -bis(benzyl)-N,N 0 -diaza-18-crown-6 and N,N 0 -bis(4-methoxybenzyl)-N,N 0 -diaza-18-crown-6 as well as with azacycles. 13,15 The conformationally flexible 18C6 and its dicyclohexyl-substituted analogues due to excess of their accessible O-atoms as H-bond acceptors provide the coordination of four dithiooxamide molecules to one CE makes it possible to expand the supramolecular architecture up to 2D layer with the second dithiooxamide molecule serving as a bridge between the (CE-dithiooxamide) n alternative chains. Based on the previously reported structures we could most probably expect the alternative chain motifs for 1-2, while two scenarios, ladder-type chain motif or extended layer seem to be possible for 3 (Scheme 2).…”