2,2′-(Heptane-1,7-di­yl)dibenz­imidazo­lium chloride nitrate monohydrate

Jin-Ping Zeng; Yun-Qian Zhang; Sai-Feng Xue; Qian-Jiang Zhu; Zhu Tao

doi:10.1107/S1600536809006370

. 2009 Feb 28;65(Pt 3):o620. doi: 10.1107/S1600536809006370

2,2′-(Heptane-1,7-diyl)dibenzimidazolium chloride nitrate monohydrate

Jin-Ping Zeng ^a, Yun-Qian Zhang ^a, Sai-Feng Xue ^a,^*, Qian-Jiang Zhu ^a, Zhu Tao ^a,^b

PMCID: PMC2968438 PMID: 21582272

Abstract

In the title compound, C₂₁H₂₆N₄ ²⁺·Cl⁻·NO₃ ⁻·H₂O, the organic cations, anions and water molecules are linked through N—H⋯Cl, N—H⋯O, N—H⋯N and O—H⋯Cl hydrogen bonds, forming a three-dimensional framework, assisted by C—H⋯π interactions.

Related literature

For general background regarding interactions of linear polyaromatic compounds with cucurbit[n]urils, see: Day & Arnold (2000 ▶); Day et al. (2002 ▶); Freeman et al. (1981 ▶); Kim et al. (2000 ▶). For the synthesis, see: Wang & Joullié (1957 ▶).

Experimental

Crystal data

C₂₁H₂₆N₄ ²⁺·Cl⁻·NO₃ ⁻·H₂O
M _r = 449.93
Orthorhombic,
a = 24.462 (10) Å
b = 5.102 (2) Å
c = 18.210 (7) Å
V = 2272.5 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.31 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.939, T _max = 0.964
14275 measured reflections
2086 independent reflections
1619 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.084
S = 1.03
2086 reflections
288 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006370/ez2159sup1.cif

e-65-0o620-sup1.cif^{(23.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006370/ez2159Isup2.hkl

e-65-0o620-Isup2.hkl^{(100.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.86	2.22	3.066 (3)	168
N2—H2A⋯O3ⁱ	0.86	1.94	2.778 (4)	164
N2—H2A⋯O1ⁱ	0.86	2.53	3.243 (4)	141
N2—H2A⋯N5ⁱ	0.86	2.59	3.436 (5)	168
N3—H3A⋯O2ⁱⁱ	0.86	1.95	2.807 (4)	177
N4—H4A⋯O1Wⁱⁱⁱ	0.86	1.87	2.730 (4)	173
O1W—H1WA⋯Cl1	0.927 (19)	2.19 (2)	3.088 (4)	163 (4)
O1W—H1WB⋯Cl1^iv	0.83 (2)	2.31 (3)	3.099 (3)	159 (5)
C10—H10A⋯Cg3^v	0.97	3.36	4.148 (4)	140
C11—H11B⋯Cg4^vi	0.97	3.21	4.047 (4)	146

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg3 and Cg4 are the centroids of the C1–C6 and C16–C21 benzene rings, respectively.

Acknowledgments

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003), the International Collaborative Project of the Ministry of Science and Technology (No. 2007400108) and the Foundation of the Governor of Guizhou Province, China.

supplementary crystallographic information

Comment

This paper describes the preparation and structure of a new linear polyaromatic compound (I) in which the multiple functional groups can develop strong intermolecular interactions with cucurbit[n]urils (CB[n]) (Freeman et al.,1981; Day & Arnold, 2000; Day et al., 2002; Kim et al., 2000).

The molecular structure of (I), shown in Fig. 1, consists of one organic cation, one Cl^- anion, one NO₃^- anion and one lattice water molecule. The two benzimidazole groups of the organic cation are not co-planar, but are oriented at a dihedral angle of 78.42 (6) ° with respect to each other. Molecules are linked via an N1—H1A···Cl1, N2—H2A···O3, N2—H2A···O1, N2—H2A···N5, N3—H3A···O2, N4—H4A···O1W and O1W—H1WA···Cl1 network of hydrogen bonds (Table 1) forming a three-dimensional framework. In addition, C—H···π interactions occur between adjacent organic cations (Table 1, Cg(3) and Cg(4) are the centroids of the C1—C6 and C16—C21 benzene rings, respectively).

Experimental

A solution of o-phenylenediamine (5.40 g, 0.05 mol) and azelaic acid (4.71 g, 0.025 mol) were refluxed for twelve hours in 50 ml of 4M HCl. The reaction mixture was then cooled for one day and the blue crystalline 2,2'-(Heptane-1,7-diyl)dibenzimidazolium dihydrochloride which separated was removed by filtration and dried (Wang et al., 1957). Yield: 31%. The dihydrochloride (2.03 g, 5 mmol) and lanthanum nitrate (3.25 g, 10 mmol) were refluxed for three h in 50 ml water, and the mixture was cooled and filtered. Upon standing at room temperature, crystals of title compound (I) were obtained after several days.