Hemi(4,4′-bipyridinium) hexa­fluorido­phosphate bis­(4-amino­benzoic acid) 4,4′-bipyridine monohydrate

Wu, Y.-Y.; Huang, C.-D.; Huang, J.-X.; Zeng, R.-H.; Luo, Y.-F.

doi:10.1107/S1600536808043900

Volume 65
Part 2
Page o278
February 2009

Received 11 December 2008
Accepted 25 December 2008
Online 10 January 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.066
wR = 0.205
Data-to-parameter ratio = 15.7
Details

Hemi(4,4'-bipyridinium) hexafluoridophosphate bis(4-aminobenzoic acid) 4,4'-bipyridine monohydrate

Yi-Yi Wu,^a Chun-De Huang,^a Jie-Xuan Huang,^a Rong-Hua Zeng ^a,^b ^* and Yi-Fan Luo ^a

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and ^bKey Laboratory of Electrochemical Technology on Energy Storage and Power Generation in Guangdong Universities, Guangzhou 510631, People's Republic of China
Correspondence e-mail: zrh321@yahoo.com.cn

In the title compound, 0.5C₁₀H₁₀N₂²⁺·PF₆^-·C₁₀H₈N₂·2C₇H₇NO₂·H₂O, the cation is located on a center of symmetry. The crystal structure is determined by a complex three-dimensional network of intermolecular O-HO, O-HN, N-HN and N-HF hydrogen bonds. [pi] - [pi] stacking interactions between neighboring pyridyl rings are also present; the centroid-centroid distance is 3.643 (5) Å. The hexafluoridophosphate anion is disordered over two positions with site-occupancy factors of ca 0.6 and 0.4.

Related literature

For the use of 4-aminobenzoic acid and 4,4'-bipyridine for the construction of three-dimensional network motifs, see: Hu et al. (2003); Yang et al. (2004).

Experimental

Crystal data

0.5C₁₀H₁₀N₂²⁺·PF₆^-·C₁₀H₈N₂·2C₇H₇NO₂·H₂O
M_r = 672.54
Triclinic, $[P \overline 1]$
a = 10.1032 (2) Å
b = 10.1142 (2) Å
c = 16.8906 (3) Å
= 92.557 (1)°
= 98.063 (1)°
= 117.346 (1)°
V = 1506.23 (5) Å³
Z = 2
Mo K radiation
= 0.18 mm^-1
T = 296 (2) K
0.18 × 0.15 × 0.14 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: none
22618 measured reflections
7121 independent reflections
3129 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.205
S = 1.02
7121 reflections
454 parameters
43 restraints
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H2WO4ⁱ	0.89	1.87	2.751 (3)	169
O1W-H1WO2ⁱⁱ	0.79	2.01	2.799 (3)	174
O3-H3AN3ⁱⁱⁱ	0.82	1.87	2.686 (3)	174
O1-H1O1W^iv	0.82	1.80	2.617 (3)	173
N1-H1BF3	0.86	2.57	3.324 (4)	147
N5-H27N4	0.86	1.84	2.700 (4)	176
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+1; (iii) x+1, y, z-1; (iv) x, y, z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); 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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2299 ).

Acknowledgements

The authors acknowledge South China Normal University for supporting this work.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hu, D. H., Huang, W., Gou, S. H., Fang, J. L. & Fun, H. K. (2003). Polyhedron, 22, 2661-2667.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, G. P., Wang, Z. Y. & Chen, J. T. (2004). J. Mol. Struct. 707, 223-229.

organic compounds