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The reaction of benzyl chloride with tetramethylethylenediamine (tmen) results in the formation of the quaternary diammonium dichloride trihydrate (dbtmen)Cl2⋅3H2O 1 (dbtmen is N,N'-dibenzyl- N,N,N',N'-tetramethylethylenediammonium) in good yields. 1 crystallises in the monoclinic P21/c space group and its structure consists of N,N'-dibenzyl-N,N,N',N'-tetramethylethylenediammonium dication, two chloride anions and three crystal water molecules all of which are located in general positions. The organic dication is H-bonded to the chloride anions and the crystal waters with the help of intra- and in- termolecular C-H⋅⋅⋅Cl and C-H⋅⋅⋅O interactions, while the chloride anions are linked to the crystal waters via O-H⋅⋅⋅Cl interactions. One of the crystal waters is linked through an intermolecular O-H⋅⋅⋅O bond with another water resulting in the formation of a water dimer. The O-H⋅⋅⋅Cl and O-H⋅⋅⋅O interactions between the chloride anions and water molecules lead to the formation of a five-membered {O3Cl2} cyclic dichloride containing a water dimer. The five-membered rings are linked into a chain with the aid of a O-H⋅⋅⋅Cl interaction. The organic cations are organised in zigzag fashion on either side of the chain and are further linked to the anionic water chain via weak C-H⋅⋅⋅O and C-H⋅⋅⋅Cl interactions, leading to the supramolecular organisation of the rings into a spiral-like of chain.

A spiral-like chain from a hydrogen-bonded cyclic dichloride containing a water dimer in a quaternary diammonium dichloride trihydrate