Source of materialThe 1-butyl-3-cyclododecyloxymethylimidazolium chloride was prepared by the reaction of 1-butylimidazole and chloromethylcyclododecyl ether in anhydrous benzene according to the procedure described in [1]. Chloromethylcyclododecyl ether was prepared by passing HCl gas through a mixture of formaldehyde and cyclododecanol [2]. Colorless plate-like crystals of the title compound were obtained by slow evaporation from a solution in ethyl acetate/methanol (10:1, v/v) at room temperature.
Experimental detailsThe hydrogen atoms participating in DH···A hydrogen interactions were refined (D = O, C; A = Cl, O).
DiscussionThe aim of the X-ray analysis of 1-butyl-3-cyclododecyloxymethylimidazolium chloride was defining the influence of quaternization of imidazole ring and anion-cation interaction on the molecule conformation.The title compound crystallizes with one molecule of water. Strong hydrogen bonds were formed between chloride anions and water molecules. These interactions lead to closed planar Cl···H1WOH2W···Cl(x,y+1,z+1)···H2WOH1W···Cl systems bonded with the cation part by hydrogen bond between chloride anion and H2 atom located at the acid carbon atom in imidazolium ring (d(C2···Cl) = 3.396(3) Å and ÐC2H2A···Cl = 159.9(3)°). Formation of this hydrogen bond results in averaged N1C2 and C2N2 bonds of 1.318(4) Å and 1.317(4) Å, respectively. The 1-butyl and 3-cyclododecyloxymethyl substituent groups have eclipsed conformation. The imidazolium rings are parallel to each other and to the b axis. Channels along a axis arise from the chloride anions surrounded by water molecules. The OH···Cl bonds, intermolecular CH···O and CH···Cl interactions are responsible for 2D layers parallel (001). Similar structural elements occur in crystal structures of quaternary ammonium and imidazolium chlorides. Channels filled by chains of chloride anions and water molecules [5,6], alternating lipophilic and hydrophilic domains [6] and double bilayers [7] were found.Z. Kristallogr.
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