Adipic acid–2,6-bis­(1H-benzimidazol-2-yl)pyridine–water (1/2/4)

Lin, S.; Jia, R.; Gao, F.; Zhou, X.

doi:10.1107/S1600536812047861

Volume 68
Part 12
Page o3457
December 2012

Received 19 October 2012
Accepted 21 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.163
Data-to-parameter ratio = 12.8
Details

Adipic acid-2,6-bis(1H-benzimidazol-2-yl)pyridine-water (1/2/4)

Songzhu Lin,^a ^* Ruokun Jia,^a Feng Gao ^a and Xiaoqing Zhou ^a

^aNortheast Dianli University, Jilin 132012, People's Republic of China
Correspondence e-mail: songzhulin@hotmail.com

The asymmetric unit of the title hydrated co-crystal, 2C₁₉H₁₃N₅·C₆H₁₀O₄·4H₂O, consists of one 2,6-bis(1H-benzimidazol-2-yl)pyridine molecule, half of an adipic acid molecule (bisected by an inversion center) and two water solvates. In the crystal, N-HO, O-HO and O-HN hydrogen bonds and [pi] - [pi] interactions [centroid-centroid distances = 3.769 (2) and 3.731 (2) Å] form a three-dimensional supramolecular structure.

Related literature

For related structures, see: Boca et al. (2000); Chetia & Iyer (2006, 2007); Xiao et al. (2010); Freire et al. (2003); Lin et al. (2012).

Experimental

Crystal data

2C₁₉H₁₃N₅·C₆H₁₀O₄·4H₂O
M_r = 840.90
Triclinic, $[P \overline 1]$
a = 9.0709 (18) Å
b = 9.6882 (19) Å
c = 12.311 (3) Å
= 88.93 (3)°
= 83.12 (3)°
= 75.14 (3)°
V = 1038.1 (4) Å³
Z = 1
Mo K radiation
= 0.10 mm^-1
T = 295 K
0.25 × 0.18 × 0.16 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
10214 measured reflections
4705 independent reflections
3555 reflections with I > 2(I)
R_int = 0.024
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.163
S = 1.15
4705 reflections
368 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H4O2W	0.95 (2)	2.16 (2)	3.084 (2)	163.3 (18)
N4-H5O2W	0.88 (2)	2.08 (2)	2.945 (2)	167.6 (18)
O1-H1N5	0.87 (1)	1.83 (1)	2.6731 (19)	163 (2)
O1W-H1WAN1ⁱ	0.85 (1)	1.99 (1)	2.8169 (18)	162 (2)
O1W-H1WBO2ⁱⁱ	0.85 (1)	1.99 (1)	2.815 (2)	165 (2)
O2W-H2WBO1Wⁱⁱⁱ	0.86 (1)	2.05 (1)	2.898 (2)	170 (3)
O2W-H2WAO1W^iv	0.87 (1)	2.01 (1)	2.867 (2)	171 (3)
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z+1; (iii) -x, -y+1, -z+1; (iv) x, y+1, z-1.

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, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2486 ).

Acknowledgements

The authors would like to thank the National Natural Science Foundation of China (51003010), the Natural Science Foundation of Jilin Province (201115178) and the Science and Technology Development Project of Jilin Province (SKLSSM201132).

References

Boca, M., Valigura, D., Svoboda, I., Fuess, H. & Linert, W. (2000). Acta Cryst. C56, 838-839.
Chetia, B. & Iyer, P. K. (2006). Tetrahedron Lett. 47, 8115-8117.
Chetia, B. & Iyer, P. K. (2007). Tetrahedron Lett. 48, 47-50.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Freire, E., Baggio, S., Muñoz, J. C. & Baggio, R. (2003). Acta Cryst. C59, o259-o262.
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.
Lin, S., Jia, R. & He, A. (2012). Acta Cryst. E68, o1820.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xiao, H., Wang, G. & Jian, F. (2010). Acta Cryst. C66, o446-o448.

organic compounds