Glutaric acid–2-(pyridin-4-yl)-1H-benzimidazole (1/1)

Songzhu Lin; Ruokun Jia; Aimin He; Xiaoli Gao

doi:10.1107/S1600536811049695

. 2011 Nov 30;67(Pt 12):o3463. doi: 10.1107/S1600536811049695

Glutaric acid–2-(pyridin-4-yl)-1H-benzimidazole (1/1)

Songzhu Lin ^a,^*, Ruokun Jia ^a, Aimin He ^a, Xiaoli Gao ^a

PMCID: PMC3239091 PMID: 22199939

Abstract

The crystal structure of the title co-crystal, C₁₂H₉N₃·C₅H₈O₄, N—H⋯O and O—H⋯N hydrogen bonds link the components. There are also π–π stacking interactions between the imidazole rings, between the imidazole and pyridine rings and between the pyridine and benzene rings [centroid–centroid distances = 3.643 (2), 3.573 (2) and 3.740 (1)Å, respectively].

Related literature

For background to hydrogen bonds, see: Moorthy et al. (2002 ▶); Muthuraman et al. (2000 ▶); Nangia & Desiraju (1999 ▶); Bhattacharjya et al. (2004 ▶). For related structures, see: Bei et al. (2000 ▶); Ozbey et al. (1998 ▶).

Experimental

Crystal data

C₁₂H₉N₃·C₅H₈O₄
M _r = 327.34
Triclinic,
a = 7.4384 (15) Å
b = 8.9911 (18) Å
c = 11.868 (2) Å
α = 86.67 (3)°
β = 81.66 (3)°
γ = 85.57 (3)°
V = 782.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.20 × 0.17 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
6041 measured reflections
2664 independent reflections
1657 reflections with I > 2σ(I)
R _int = 0.024
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.149
S = 1.11
2664 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049695/fj2466sup1.cif

e-67-o3463-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049695/fj2466Isup2.hkl

e-67-o3463-Isup2.hkl^{(130.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811049695/fj2466Isup3.cml

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⋯O2ⁱ	0.86	2.10	2.957 (3)	176
O1—H2⋯N3ⁱⁱ	0.87 (1)	1.75 (1)	2.615 (3)	173 (4)
O4—H1⋯N2	1.02 (4)	1.71 (4)	2.686 (3)	158 (3)

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

Acknowledgments

The authors would like to thank the National Natural Science Foundation of China (51003010) and the Natural Science Foundation of Jilin Province (201115178).

supplementary crystallographic information

Comment

The strong (O—H···O) and weak (C—H···O) hydrogen bonds, the halogen bond (C—X···O) and the weak C—H···π interaction, have been well characterized and exploited in the design of molecular assemblies (Moorthy et al., 2002; Muthuraman et al., 2000; Nangia and Desiraju, 1999; Bhattacharjya et al., 2004). Our interest in benzimidazole stems from their biological activity (Bei et al., 2000; Ozbey et al., 1998). In this paper, we sysnthesized the title compound and report its structure.

Scheme I

The compound consists of 2-(pyridin-4-yl)-1H-benzimidazole and glutaric acid. In the title compound, the dihedral angle between the imidazole and the benzene was 1.40 (2)°, while the benzimidazole and the pyridine was 5.25 (1)°. It results that the all atoms in the 2-(pyridin-4-yl)-1H-benzimidazole are not coplanar strictly. In the part of glutaric acid, four atoms O1, O2, C13, C14 are lying in a same plane (p1) with the maximum diviation of 0.002° for C13, while other four atoms O3, O4, C16, C17 lying in another plane (p2) with the maximum diviation of 0.001% for O3. The dihedral angle between p1 and p2 is 10.50 (2)°.

In the lattice, there exist some kinds of hydrogen bonds. It forms one-dimension stairway structure between 2-(pyridin-4-yl)-1H-benzimidazole and glutaric acid via N—H···O, O—H···N hydrogen bonds (figure 2a and 2 b). Two adjacent strairway chains formed two dimension structure via the C—H···O intermolecular interaction.

In addition, there exists some π–π interactions between the rings [Cg1···Cg1=3.643 (2), Cg1···Cg2= 3.573 (2) and Cg2···Cg3=3.740 (1), respectively (Cg1, Cg2, Cg3 refer to the centroid of imidazole N1, C1, C6, N2, C7; the pyridine N3, C8, C9, C10, C11, C12 and the phenyl ring C1, C2, C3, C4, C5, C6, respectively)]. The π–π interaction, as well as the inter- and intra- hydrogen bond stabilized the crystal structure.

Experimental

The title compound was obtained by 2-Pyridin-4-yl-1H-benzoimidazole (0.020 g, 0.1 mmol) and glutaric acid (0.013 g, 0.1 mmol) dissolved in 30 ml solution mixed with ethanol and water by 2:1(V/V) was heated to refluxed for 6 h and cooled to the room temperature. Single crystals suitable for x-ray measurements were obtained by recrystallization at room temperature.