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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 [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.163
Data-to-parameter ratio = 12.8
Details
Open access

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

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-H...O, O-H...O and O-H...N 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[Boca, M., Valigura, D., Svoboda, I., Fuess, H. & Linert, W. (2000). Acta Cryst. C56, 838-839.]); Chetia & Iyer (2006[Chetia, B. & Iyer, P. K. (2006). Tetrahedron Lett. 47, 8115-8117.], 2007[Chetia, B. & Iyer, P. K. (2007). Tetrahedron Lett. 48, 47-50.]); Xiao et al. (2010[Xiao, H., Wang, G. & Jian, F. (2010). Acta Cryst. C66, o446-o448.]); Freire et al. (2003[Freire, E., Baggio, S., Muñoz, J. C. & Baggio, R. (2003). Acta Cryst. C59, o259-o262.]); Lin et al. (2012[Lin, S., Jia, R. & He, A. (2012). Acta Cryst. E68, o1820.]).

[Scheme 1]

Experimental

Crystal data
  • 2C19H13N5·C6H10O4·4H2O

  • Mr = 840.90

  • Triclinic, [P \overline 1]

  • a = 9.0709 (18) Å

  • b = 9.6882 (19) Å

  • c = 12.311 (3) Å

  • [alpha] = 88.93 (3)°

  • [beta] = 83.12 (3)°

  • [gamma] = 75.14 (3)°

  • V = 1038.1 (4) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.024

  • 3 standard reflections every 100 reflections intensity decay: none

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H4...O2W 0.95 (2) 2.16 (2) 3.084 (2) 163.3 (18)
N4-H5...O2W 0.88 (2) 2.08 (2) 2.945 (2) 167.6 (18)
O1-H1...N5 0.87 (1) 1.83 (1) 2.6731 (19) 163 (2)
O1W-H1WA...N1i 0.85 (1) 1.99 (1) 2.8169 (18) 162 (2)
O1W-H1WB...O2ii 0.85 (1) 1.99 (1) 2.815 (2) 165 (2)
O2W-H2WB...O1Wiii 0.86 (1) 2.05 (1) 2.898 (2) 170 (3)
O2W-H2WA...O1Wiv 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[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989[Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: WinGX (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.].


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


Acta Cryst (2012). E68, o3457  [ doi:10.1107/S1600536812047861 ]

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