2,6-Bis(1H-benzimidazol­-2-yl)pyridine methanol trisolvate

Ying Chen; Jixi Guo; Xingcai Huang; Ruirui Yun; Huilu Wu

doi:10.1107/S1600536809012574

. 2009 Apr 10;65(Pt 5):o1013. doi: 10.1107/S1600536809012574

2,6-Bis(1H-benzimidazol-2-yl)pyridine methanol trisolvate

Ying Chen ^a, Jixi Guo ^b, Xingcai Huang ^a, Ruirui Yun ^a, Huilu Wu ^a,^*

PMCID: PMC2977700 PMID: 21583836

Abstract

In the title compound, C₁₉H₁₃N₅·3CH₄O, the 2,6-bis(2-benzimidazolyl)pyridine molecule is essentially planar with an r.m.s. deviation for all non-H atoms of 0.185 Å. The crystal structure is stabilized by intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds and weak π⋯π stacking interactions with centroid–centroid distances of 3.6675 (16) and 3.6891 (15) Å. The atoms of one of the methanol solvent molecules are disordered over two sites with refined occupancies of 0.606(8) and 0.394(8).

Related literature

For the crystal structures of the mono- and sesquihydrate analogs of 2,6-bis(2-benzimidazolyl)pyridine, see: Freire et al. (2003 ▶). For the synthesis of 2,6-bis(2-benzimidazolyl)pyridine, see: Addison & Burke (1981 ▶).

Experimental

Crystal data

C₁₉H₁₃N₅·3CH₄O
M _r = 407.47
Monoclinic,
a = 11.2686 (9) Å
b = 15.0928 (13) Å
c = 13.0679 (11) Å
β = 107.391 (2)°
V = 2120.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 153 K
0.18 × 0.14 × 0.11 mm

Data collection

Rigaku R-AXIS Spider diffractometer
Absorption correction: multi-scan (Higashi, 1995 ▶) T _min = 0.984, T _max = 0.990
17035 measured reflections
3945 independent reflections
2527 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.077
wR(F ²) = 0.236
S = 1.04
3945 reflections
307 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: RAPID-AUTO (Rigaku/MSC 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012574/lh2799sup1.cif

e-65-o1013-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012574/lh2799Isup2.hkl

e-65-o1013-Isup2.hkl^{(193.4KB, 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
O1—H1⋯O2ⁱ	0.84	1.83	2.670 (3)	176
O2—H2⋯N4	0.84	1.91	2.741 (3)	168
N1—H1N⋯O1	0.866 (10)	2.069 (12)	2.927 (3)	171 (3)
N3—H3N⋯O1	0.863 (10)	2.069 (12)	2.925 (3)	171 (4)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support and a grant from ‘Qing Lan’ Talent Engineering Funds and Students’ Science and Technology Innovation Funds (grant No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and Long Yuan ‘Qing Nian’ of Gansu Province is also acknowledged.

supplementary crystallographic information

Comment

The synthesis of 2,6-bis(2-benzimidazolyl)pyridine has been reported in the literature (Addison & Burke 1981) and the crystal structures of the mono and sesqihydrates of this compound have been determined (Freire et al., 2003). During our studies of benzimidazole complexes involving a recrystallization of 2,6-bis(2-benzimidazolyl)pyridine from methanol we unexpectedly form the trimethanol solvate (I).

The molecular structure of the 2,6-bis(2-benzimidazolyl)pyridine molecule is shown in Fig. 1. The molecule is essentially planar with a rms deviation of all non-hydrogen fitted atoms = 0.185. The crystal structure is stabilized by intermolecular hydrogen bonds (see Table 1) and weak π···π stacking interactions (Fig. 2) with, centroid to centroid distances of 3.6675 (16) and 3.6891 (15)Å, between pryridine rings and benzimidazole rings of inversion related molecules.

Experimental

2,6-bis(2-benzimidazolyl)pyridine was prepared by the method of Addison & Burke (1981). After recrystallization from methanol, fine white needles were formed. The mother liquor was set aside for several days leading to the formation of crystals that were suitable for X-ray diffraction analysis.