2′,6′-Bis(4-carb­oxy­phen­yl)-4,4′-bipyridin-1-ium nitrate 0.25-hydrate

Li, Y.; Zang, H.; Su, G.

doi:10.1107/S1600536811051506

Volume 68
Part 1
Page o43
January 2012

Received 22 November 2011
Accepted 30 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.050
wR = 0.150
Data-to-parameter ratio = 13.2
Details

2',6'-Bis(4-carboxyphenyl)-4,4'-bipyridin-1-ium nitrate 0.25-hydrate

Yaping Li,^a Hu Zang ^b ^* and Guanfang Su ^a

^aDepartment of Ophthalmology, The Second Hospital of Jilin University, Changchun 130041, People's Republic of China, and ^bDepartment of Orthopedics, The China-Japan Union Hospital of Jilin University, Changchun 130033, People's Republic of China
Correspondence e-mail: doctorzang@163.com

In the title compound, C₂₄H₁₇N₂O₄⁺·NO₃^-·0.25H₂O, the central pyridine ring of the 2',6'-bis(4-carboxyphenyl)-4,4'-bipyridin-1-ium cation is almost coplanar with one benzene ring [dihedral angle = 1.03 (5)°], while it makes dihedral angles of 9.59 (5)° with the other benzene ring and 13.66 (6)° with the pyridinium ring. In the crystal, N-HO and O-HO hydrogen bonds link the cations and nitrate anions into a sheet in the (302) plane. The crystal structure also exhibits [pi] - [pi] interactions between the central pyridine ring and the benzene rings of neighboring molecules [centroid-centroid distance = 3.6756 (13) Å].

Related literature

For the properties and applications of molecular-ionic crystals, see: Katrusiak & Szafranski (2006); Liao et al. (2008); Wang (2010).

Experimental

Crystal data

C₂₄H₁₇N₂O₄⁺·NO₃^-·0.25H₂O
M_r = 463.91
Monoclinic, P 2₁ /c
a = 13.6978 (11) Å
b = 16.0688 (12) Å
c = 9.6354 (8) Å
= 92.696 (1)°
V = 2118.5 (3) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 293 K
0.25 × 0.21 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.973, T_max = 0.978
11529 measured reflections
4158 independent reflections
2605 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.150
S = 1.04
4158 reflections
316 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O5ⁱ	0.86	1.84	2.697 (2)	171
O2-H2AO3ⁱⁱ	0.82	1.93	2.728 (2)	163
O4-H4O5	0.82	1.78	2.598 (2)	173
O1W-H1AO1Wⁱⁱⁱ	0.92	2.14	2.963 (18)	149
O1W-H1BO1^iv	0.90	2.22	3.059 (8)	154
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5723 ).

Acknowledgements

The authors thank Jilin University for supporting this work.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Katrusiak, A. & Szafranski, M. (2006). J. Am. Chem. Soc. 128, 15775-15785.
Liao, C. Y., Chan, K. T., Chiu, P. L., Chen, C. Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973-2978.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, B. (2010). Acta Cryst. E66, o1473.

organic compounds