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

Chen, Y.; Guo, J.; Huang, X.; Yun, R.; Wu, H.

doi:10.1107/S1600536809012574

Volume 65
Part 5
Page o1013
May 2009

Received 28 March 2009
Accepted 3 April 2009
Online 10 April 2009

Key indicators
Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.077
wR = 0.236
Data-to-parameter ratio = 12.9
Details

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

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

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bInstitute of Applied Chemistry, Xinjiang University, Urumqi 830046, Xinjiang, People's Republic of China
Correspondence e-mail: wuhuilu@163.com

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-HO, O-HN and N-HO hydrogen bonds and weak [pi] [pi] 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, P 2₁ /n
a = 11.2686 (9) Å
b = 15.0928 (13) Å
c = 13.0679 (11) Å
= 107.391 (2)°
V = 2120.9 (3) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.077
wR(F²) = 0.236
S = 1.04
3945 reflections
307 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.39 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.84	1.83	2.670 (3)	176
O2-H2N4	0.84	1.91	2.741 (3)	168
N1-H1NO1	0.866 (10)	2.069 (12)	2.927 (3)	171 (3)
N3-H3NO1	0.863 (10)	2.069 (12)	2.925 (3)	171 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: LH2799 ).

Acknowledgements

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.

References

Addison, A. W. & Burke, P. J. (1981). J. Heterocycl. Chem. 18, 803-805.
Freire, E., Baggio, S., Muñoz, J. C. & Baggio, R. (2003). Acta Cryst. C59, o259-o262.
Higashi, T. (1995). Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC, The Woodlans, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds