1-(2-Cyano­ethyl)-2-(2-pyrid­yl)-1H,3H-benzimidazol-3-ium perchlorate

Yan Li; Xiaoliang Tang; Jiayu Chen; Daxiang Wu; Weisheng Liu

doi:10.1107/S1600536809055251

. 2010 Jan 20;66(Pt 2):o413. doi: 10.1107/S1600536809055251

1-(2-Cyanoethyl)-2-(2-pyridyl)-1H,3H-benzimidazol-3-ium perchlorate

Yan Li ^a,^b, Xiaoliang Tang ^a, Jiayu Chen ^a, Daxiang Wu ^a, Weisheng Liu ^a,^*

PMCID: PMC2979728 PMID: 21579831

Abstract

The title compound, C₁₅H₁₃N₄ ⁺·ClO₄ ⁻, comprises a nonplanar 1-(2-cyanoethyl)-2-(2-pyridyl)-1H,3H-benzimidazol-3-ium cation [dihedral angle between the imidazole and pyridine rings = 22.5 (8)°] and a perchlorate anion. The cation is formed by protonation of the N atom of the benzimidazole ring. A charged N—H⋯O hydrogen bond connects the anion and cation, and intermolecular C—H⋯O and C—H⋯N interactions contribute to the crystal packing.

Related literature

For the pharmacological activity of benzimidazole and its derivatives, see: Feng & Xu (2001 ▶); Ferey (2001 ▶); Hossain et al. (2001 ▶); Howarth & Hanlon (2001 ▶); Kazak et al. (2006 ▶); Li et al. (1998 ▶).

Experimental

Crystal data

C₁₅H₁₃N₄ ⁺·ClO₄ ⁻
M _r = 348.74
Triclinic,
a = 8.788 (1) Å
b = 9.4608 (10) Å
c = 10.6013 (11) Å
α = 69.690 (2)°
β = 73.844 (2)°
γ = 86.193 (2)°
V = 793.52 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.22 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.940, T _max = 0.955
4167 measured reflections
2924 independent reflections
2316 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.122
S = 1.01
2924 reflections
221 parameters
102 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055251/kp2242sup1.cif

e-66-0o413-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055251/kp2242Isup2.hkl

e-66-0o413-Isup2.hkl^{(143.5KB, 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
N2—H5⋯O4	0.77 (3)	2.11 (3)	2.885 (4)	179 (4)
C11—H11⋯O3	0.93	2.54	3.343 (5)	145
C4—H4⋯O4	0.93	2.62	3.347 (4)	135
C13—H13A⋯N1	0.97	2.41	2.903 (4)	111
C10—H10⋯N4ⁱ	0.93	2.64	3.423 (4)	142
C13—H13B⋯O2ⁱⁱ	0.97	2.60	3.427 (4)	144
C14—H14B⋯O2ⁱⁱⁱ	0.97	2.57	3.483 (4)	157
C2—H2⋯O1^iv	0.93	2.62	3.552 (4)	180

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors thank the National Natural Science Foundation of China (20771048, 20931003, 20621091, J0730425) for financial support.

supplementary crystallographic information

Comment

For many years benzimidazole and its derivatives continue to attract attention in chemical synthesis, structural science and applied biological research due to their various pharmacological activities (Li et al., 1998; Howarth & Hanlon, 2001; Feng & Xu, 2001; Ferey, 2001; Kazak et al., 2006). Like the phenanthroline based ligands these compounds are known to chelate metal atoms although their coordination chemistry has not been as extensively explored. To further widen the scope of research on the chemical and physical properties of benzimidazole derivatives, there is a need to prepare a new series of benzimidazole derivatives. In this paper, we present the structure of the title compound as a perchlorate salt.

The compound is composed of C₁₅H₁₃N₄⁺ cation and a perchlorate anion, in a 1:1 ratio (Fig. 1). In C₁₅H₁₃N₄⁺ cation, the molecular skeleton of protonated 2-(2-pyridyl)benzimidazole is non-planar and the dihedral angle between benzimidazole ring and pyridine ring is 25.46°. Two of O atoms of the perchlorate anion, link benzimidazole via the charged N(2)–H(5)···O(4) and C(11)–H(11)···O(3) hydrogen bonds (Table 1). In addition, intermolecular C–H···O, N–H···O hydrogen bonds and π···π interactions between benzimidazole groups [Cg···Cgⁱ plane···plane separation = 3.6933 (16) Å, i = 1 - x, 1 - y, 1 - z] link the molecules into a three-dimensional structure (Fig. 2).

Experimental

The ligand, 1-(cyanoethyl)-2-(2-pyridyl)benzimidazole was prepared according to the method described by Hossain et al. (2001), using 2-(2-pyridyl)benzimidazole and acrylonitrile as starting materials (yield: 62%, m.p. 378–383 K).

Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of a methanol solution (6 ml) containing Fe(ClO₄)₃.10H₂O (26.7 mg, 0.05 mmol) and 1-(cyanoethyl)-2-(2-pyridyl)benzimidazole (24.8 mg, 0.10 mmol) after two weeks at room temperature. Our attempt to obtain an iron(III) perchlorate complex of the ligand failed and, instead, the protonated ligand salt was crystallised.