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

Abstract

The reaction of benzyl chloride with tetramethylethylenediamine (tmen) results in the formation of the quaternary diammonium dichloride trihydrate (dbtmen)Cl 2 ⋅3H 2 O 1 (dbtmen is N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium) in good yields. 1 crystallises in the monoclinic P2 1 /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 intermolecular 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 {O 3 Cl 2 } 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.

N,N′-Dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide dihydrate

“…For related literature, see: Chen et al (2006); Jayaraman et al (2002); Kabak et al (2000); Li et al (2006); Mathew et al (2002); Misra et al (2007); Nastase et al (2007); Pan et al (2007); Srinivasan et al (2003Srinivasan et al ( , 2005Srinivasan et al ( , 2007.…”

“…Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97. It is well known that organic amines, such as ethylenediamine (en), 1,3-propanediamine (1,3-pnen), N,N,N′,N′-tetramethylethylenediamine (tmen), piperazine (pip), etc, have been widely used as structure-directing agents for the construction of novel supramolecular assemblies (Misra et al, 2007, Nastase et al, 2007, Pan et al, 2007, Srinivasan et al, 2007, Li et al, 2006, Chen et al, 2006, Mathew et al, 2002, Jayaraman et al, 2002, Kabak et al, 2000. In a search for more organic surpramolecur amines, we have synthesized the title compound, (I), the structure of which is presented in this paper.…”

Synthesis, spectroscopy and supramolecular structures of two magnesium 4-nitrobenzoate complexes

“…(iii) -x, -y, -z + 1; (iv) x, y -1, z -1; (v) x -1, y -1, z water dimer in 2 are shorter than the sum of their van der Waals radii but longer than the reported values for nearly linear water dimers identified in other crystalline environments [37][38][39] and the inbuilt cyclic water dimer. 40 Interestingly the OHO angle of 165° which indicates a strong interaction, is more than the reported value of 160 o for the inbuilt cyclic water dimer.…”

“…[33][34][35] In recent years the crystallographic identification of several H-bonded water clusters 36 especially linear water dimers in crystalline hydrates has been reported. [37][38][39] The patterns of water clusters within the Cambridge Structural Database (CSD Version 5⋅23 April 2002) have been reviewed by In-fantes and Motherwell 21 and classified as discrete chains and rings, infinite chains and tapes, and layer structures. According to this classification many of the reported water clusters fall in the category of discrete chains with water dimers accounting for the majority of the structures.…”