From 1D strands to extended molecular assemblies in the binary compounds of dithiooxamide and dithiobiurea with crown ethers

Abstract

The hydrogen-bonding networks for seven new binary compounds of dithiooxamide, (NH2CS)2 (dtox) and dithiobiurea (NH2CSNH)2 (dtur) with crown ethers, 18-crown-6 (18C6), 15-crown-5 (15C5), 12-crown-4 (12C4), cis-syn-cis-(DCHA), and cis-anti-cis-(DCHB) isomers of dicyclohexyl-18 -crown-6 are discussed. (15C5.dtox), (18C6.dtur) and (DCHB.dtur) afford one-dimensional hydrogen-bonded polymeric arrays where the components alternate. In (DCHA.2dtox) and (DCHB.2dtox) the similar hydrogen-bonded chains are further interlinked via dtox molecules to generate layered motifs. In (15C5.2dtur) the dtur molecules are self-assembled into layers via N-H...S hydrogen bonds. 15C5 spacers link adjacent layers into a three-dimensional network. In (12C4.dtur) the dtur molecules are arranged in chains. These chains alternate with the crown molecules attached to them through N-H...O hydrogen bonds in such a way that each 12C4 appears to be linked with four dtur molecules and vice versa thus providing a three-dimensional grid.

N,N′-Diisopentyldithiooxamide

“…The thioamide moiety is planar [maximum deviation from the mean plane for the C1 = 0.001 1 hybridized C atoms mean that the side aliphatic chains are above and below with respect to the core planar fragment. The thioamide geometrical parameters in the table are in accord with those found for similar crystal structures (Shimanouchi & Sasada, 1979;Bermejo et al, 1998;Perec et al, 1995;Jean 1994;Simonov et al 2003).…”

“…For related literature, see: Aversa et al (1997Aversa et al ( , 2000; Bermejo et al (1998); Cremer & Pople (1975); Desseyn et al (1978); Hurd et al (1961); Jean (1994); Lanza et al (2000Lanza et al ( , 2002Lanza et al ( , 2003Lanza et al ( , 2005; Perec et al (1995); Shimanouchi & Sasada (1979); Simonov et al (2003); Veit et al (1984); Ye et al (1991).…”

Crystal structure of carbazole—1,4,7,10-tetraoxacyclododecane, C12H9N·C8H16O4

“…In general the crown ethers form these compounds with stronger dipolar substrates; i. e. dithiobiurea ·1 2-crown-4 [2], 3,4-diamino-1,2,5-oxadiazole ·15-crown-5 [3], or 4-nitrosoaniline ·18-crown-6 [4]. The associate of 12-crown-4 with the less polar heterocycle carbazole, which we report here, is new and unusual.…”

1,4,7,10-Tetraoxacyclododecane–triphenylmethanethiol (1/2)

“…For more than two decades, crown ethers have been a very useful tool for following interaction pathways between neutral molecules, including biologically important pathways. As a continuation of our contribution to this topic (Simonov et al, 2003), we report here the crystal structure of the title binary adduct, (I), of triphenylmethanethiol with 1,4,7,10-tetraoxacyclododecane (12-crown-4, 12C4). Compound (I) is the ®rst example of an adduct between a thiol and a crown ether to be structurally described.…”

“…À (Simonov et al, 1993), Ph 3 SiOH (Babaian et al, 1990), (PhSO 2 ) 2 NH (Wijaya et al, 1998), (EtSO 2 ) 2 CH 2 (Michalides et al, 1995) or Me 2 CNNHC( S)NH 2 (Moers et al, 1999), and the binary adduct with dithiobisurea, (NH 2 CSNH) 2 , in a 1:1 ratio (Simonov et al, 2003). The structures of these adducts are held together by OÐHÁ Á ÁO, NÐHÁ Á ÁO or CÐHÁ Á ÁO hydrogen bonds between the respective substrate and 12C4.…”