1-Methyl-2-({[(1-methyl-1H-benzimid­azol-2-yl)meth­yl](phen­yl)amino}­meth­yl)1H-benzimidazol-3-ium picrate

Bin Liu; Fan Kou; Fei Jia; Jingkui Yuan; Huilu Wu

doi:10.1107/S1600536811024275

. 2011 Jun 25;67(Pt 7):o1816. doi: 10.1107/S1600536811024275

1-Methyl-2-({[(1-methyl-1H-benzimidazol-2-yl)methyl](phenyl)amino}methyl)1H-benzimidazol-3-ium picrate

Bin Liu ^a, Fan Kou ^a, Fei Jia ^a, Jingkui Yuan ^a, Huilu Wu ^a,^*

PMCID: PMC3151771 PMID: 21837185

Abstract

In the title molecular salt, C₂₄H₂₄N₅ ⁺·C₆H₂N₃O₇ ⁻, the dihedral angle between the benzimidazole rings of the cation is 5.041 (2)°. In the anion, the three nitro groups make dihedral angles of 2.468 (3), 12.795 (3) and 24.958 (4)° with respect to the central ring. In the crystal, weak aromatic π–π stacking [centroid–centroid distance = 3.599 (15) Å] consolidates the packing. In addition, an intramolecular N—H⋯N hydrogen bond is observed.

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008 ▶) and to benzimidazoles, see: Ram et al. (1992 ▶). For the biological activivity of benzimidazoles, see: Baraldi et al. (2004 ▶); Göker et al. (2002 ▶); Jayasekera et al. (2005 ▶); Starčević et al. (2007 ▶).

Experimental

Crystal data

C₂₄H₂₄N₅ ⁺·C₆H₂N₃O₇ ⁻
M _r = 610.59
Triclinic,
a = 9.4233 (5) Å
b = 12.3523 (7) Å
c = 12.5772 (7) Å
α = 92.007 (1)°
β = 98.497 (1)°
γ = 103.685 (1)°
V = 1403.07 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.31 × 0.30 × 0.29 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.968, T _max = 0.970
11689 measured reflections
5217 independent reflections
3567 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.221
S = 1.19
5217 reflections
411 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811024275/lr2014sup1.cif

e-67-o1816-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024275/lr2014Isup2.hkl

e-67-o1816-Isup2.hkl^{(255.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811024275/lr2014Isup3.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
N3—H3N⋯N1	0.92	1.85	2.715 (8)	157

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Acknowledgments

The authors acknowledge the financial support and grants from the ‘Qing Lan’ Talent Engineering Funds and Students’ Science and Technology Innovation Funds (grant No. DXS2010–040) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and the Long Yuan ‘Qing Nian’ of Gansu Province is also acknowledged.

supplementary crystallographic information

Comment

Bis-benzimidazoles are known to be strong chelating agents coordinating through both the C=N nitrogen atoms. In addition, bis-benzimidazoles have a polymer-forming characteristic as a typical multidentate ligand. Benzimidazole compounds are environmentally friendly compounds with two high active nitrogen atoms in 1, 3-sites (Ram et al., 1992). Benzimidazoles and their azino-fused cyclic derivatives have a wide range of well known biological activities such as anticancer (Baraldi et al., 2004), antimicrobial (Jayasekera et al., 2005), antifungal (Göker et al., 2002), antiviral (Starčević et al., 2007).

In this paper, the asymmetric unit of the title proton transfer compound consists of a bis(N-methylbenzimidazol-2-ylmethyl)aniline(MEBBA) cation interacting with a picrate anion. The proton of the picric acid is transfered to the N3 nitrogen atoms of the MEBBA(Fig. 1). The dihedral angle between the planes defined by N2—C7—N1 and N3—C10—N4 is 5.041 (2)°, which indicates that the two benzimidazole rings are almost coplanar.

The crystal structure is mainly stabilized by weak π–π interactions involving the benzimidazol rings with centroid-centroid distances, Cg1 ··· Cg 3ⁱ and Cg2 ···Cg4ⁱ of 3.5999 (15) and 4.017 (18) Å repectively [symmetry code: (i) 1-x,1-y,1-z. Cg1 centroid of the (N1,C1,C6,N2,C7) ring; Cg2 centroid of the (N3,C10,N4.C11,C16) ring; Cg3 centroid of the (C11-C16) ring; Cg4 centroid of the (C1-C6) ring ]. In addition an N3-H3N···N1 intramolecular hydrogen bond is observed.