2,2′-(Decane-1,10-di­yl)dibenz­imid­azo­lium dichloride trihydrate

Jun-Ming Yi; Yun-Qian Zhang; Sai-Feng Xue; Qian-Jiang Zhu

doi:10.1107/S160053680800617X

. 2008 Mar 12;64(Pt 4):o696. doi: 10.1107/S160053680800617X

2,2′-(Decane-1,10-diyl)dibenzimidazolium dichloride trihydrate

Jun-Ming Yi ^a, Yun-Qian Zhang ^b,^*, Sai-Feng Xue ^b, Qian-Jiang Zhu ^c

PMCID: PMC2960893 PMID: 21202088

Abstract

The organic cation in the title compound, C₂₄H₃₂N₄ ²⁺·2Cl⁻·3H₂O, is situated on an inversion centre. The cations, anions and water molecules are linked via N—H⋯O, N—H⋯Cl, O—H⋯O and O—H⋯Cl hydrogen bonds and C—H⋯π interactions, forming a three-dimensional framework.

Related literature

For general background, see: Day & Arnold (2000 ▶); Day et al. (2002 ▶); Freeman et al. (1981 ▶); Kim et al. (2000 ▶); Wang & Joullie (1957 ▶).

Experimental

Crystal data

C₂₄H₃₂N₄ ²⁺·2Cl⁻·3H₂O
M _r = 501.48
Triclinic,
a = 10.8482 (6) Å
b = 11.5089 (6) Å
c = 11.9503 (6) Å
α = 77.619 (2)°
β = 71.501 (2)°
γ = 76.030 (2)°
V = 1357.58 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 (2) K
0.29 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.926, T _max = 0.958
13250 measured reflections
4702 independent reflections
3802 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.089
S = 1.06
4702 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800617X/rk2079sup1.cif

e-64-0o696-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800617X/rk2079Isup2.hkl

e-64-0o696-Isup2.hkl^{(225.6KB, 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—H1⋯O3W	0.86	1.88	2.7142 (19)	162
N2—H2A⋯O2W	0.86	1.94	2.7500 (19)	157
N3—H3A⋯O1Wⁱ	0.86	1.88	2.7322 (18)	173
N4—H4A⋯Cl2	0.86	2.25	3.0823 (15)	163
O1W—H1WA⋯Cl1ⁱⁱ	0.87	2.25	3.1027 (13)	168
O1W—H1WB⋯Cl1ⁱⁱⁱ	0.89	2.21	3.0804 (13)	166
O2W—H2WA⋯O1W	0.97	1.96	2.8763 (18)	158
O2W—H2WB⋯Cl2^iv	0.90	2.28	3.1703 (13)	170
O3W—H3WB⋯Cl1	0.93	2.20	3.0912 (13)	162
O3W—H3WA⋯Cl2	0.92	2.21	3.1229 (13)	172
C11—H11B⋯Cg2	0.97	3.17	3.847 (3)	128
C22—H22A⋯Cg1^v	0.97	2.92	3.863 (3)	165

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) . Cg1, Cg2 are the centroids of the C1–C6 and C13–C18 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

We prepared and present a new 'axle' polyaromatic compound (I) containing multiple functional groups that 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 structure of I, [C₂₄H₃₂N₄]²⁺.2Cl^-.3(H₂O), contains two independent molecules, which occupy the center of symmetry positions in the middle of C12–C12ⁱ and C24–C24ⁱⁱ bonds, respectively (symmetry codes: (i) -x + 2, -y + 3, -z, (ii) -x, -y, -z + 2). The angle between the plane of the phenyl rings and the plane through C10, C11, C12, C12ⁱ, C11ⁱ, C10ⁱ chain is 86.74 (9) Å, and the plane through C22, C23, C24, C24ⁱⁱ, C23ⁱⁱ, C22ⁱⁱ chain is 89.26 (10) Å. The cations, anions and water molecules are linked via N–H···O, N–H···Cl, O–H···O, O–H···Cl hydrogen bonds and C—H···π intreactions forming three–dimensional framework (see table, Cg1, Cg2 are the centroid of the C1/C6–benzene ring and C13/C18–benzene ring, respectively).

Experimental

A solution of o–phenylenedimine (5.40 g, 0.05 mol) and 1,10–decanedicarboxylic acid (5.80 g, 0.025 mol) were reflux for 12 h in 70 ml of 4M HCl, the reaction mixture was cooled for one day and the crystals of I was removed by filtration and dried. The crystals of the title compound suitable for X–ray diffraction were obtained by dissolving in water and standing at room temperature after several days (Wang & Joullie, 1957). Yield: 25%.