4,4′-Ethyl­enedipyridinium bis­(3,4,5-trihy­droxy­benzoate) sesquihydrate

Shen, F.M.; Lush, S.F.

doi:10.1107/S1600536810027169

Volume 66
Part 8
Pages o2056-o2057
August 2010

Received 25 June 2010
Accepted 8 July 2010
Online 17 July 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.007 Å
R = 0.099
wR = 0.221
Data-to-parameter ratio = 11.9
Details

4,4'-Ethylenedipyridinium bis(3,4,5-trihydroxybenzoate) sesquihydrate

Fwu Ming Shen ^a and Shie Fu Lush ^b ^*

^aDepartment of Biotechnology, Yuanpei University, No.306, Yuanpei St, HsinChu, Taiwan 30015, and ^bDepartment of Medical Laboratory Science Biotechnology, Yuanpei University, HsinChu, Taiwan 30015
Correspondence e-mail: lush@mail.ypu.edu.tw

The asymmetric unit of the title compound, C₁₂H₁₄N₂²⁺·2C₇H₅O₅^-·1.5H₂O, contains two 4,4'-ethylenedipyridinium cations, four gallate anions and three water molecules. In the 4,4'-ethylenedipyridinium cations, the dihedral angles between the pyridinium rings are 4.3 (3) and 18.6 (3)°. Extensive classical N-HO and O-HO hydrogen bonding and weak C-HO hydrogen bonding and C-H [pi] interactions are present in the crystal structure. [pi] - [pi] stacking is also observed, the centroid-centroid separations between the benzene and pyridine rings being 3.611 (3), 3.448 (3) and 3.536 (3) Å.

Related literature

For related structures, see: Bebout & Pagola (2009); Li & Guo (2007); Okabe et al. (2001). For the biological activity of gallic acid (3,4,5-trihydroxybenzoic acid) and its derivatives, see: Fukumoto & Mazza (2000).

Experimental

Crystal data

C₁₂H₁₄N₂²⁺·2C₇H₅O₅^-·1.5H₂O
M_r = 551.50
Triclinic, $[P \overline 1]$
a = 9.4445 (19) Å
b = 15.331 (3) Å
c = 18.307 (4) Å
= 109.88 (3)°
= 93.68 (3)°
= 92.90 (3)°
V = 2480.2 (10) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 295 K
0.32 × 0.30 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) T_min = 0.928, T_max = 1.016
26683 measured reflections
8520 independent reflections
5004 reflections with I > 2(I)
R_int = 0.104

Refinement

R[F² > 2(F²)] = 0.099
wR(F²) = 0.221
S = 1.35
8520 reflections
713 parameters
H-atom parameters constrained
_max = 0.47 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg6 and Cg8 are the centroids of the C33-C38 and C47-C52 rings, respectively.

D-HA	D-H	HA	DA	D-HA
N1-H1AO13ⁱ	0.86	1.98	2.793 (5)	158
N1-H1AO14ⁱ	0.86	2.32	2.914 (5)	127
N2-H2AO11	0.86	1.74	2.571 (5)	163
N2-H2AO12	0.86	2.60	3.297 (5)	139
N3-H3BO1ⁱⁱ	0.86	1.67	2.514 (5)	166
N4-H4CO3ⁱⁱⁱ	0.86	1.97	2.804 (5)	165
N4-H4CO4ⁱⁱⁱ	0.86	2.47	3.026 (5)	123
O3-H3AO7	0.82	1.83	2.652 (4)	175
O4-H4BO16^iv	0.82	2.06	2.804 (4)	151
O5-H5BO6^v	0.82	1.81	2.634 (5)	180
O8-H8AO21	0.82	1.90	2.715 (4)	175
O9-H9BO15^vi	0.82	2.47	3.153 (4)	141
O10-H10BO15^vi	0.82	2.12	2.812 (5)	142
O13-H13AO17^vii	0.82	1.75	2.569 (4)	172
O14-H14AO15	0.82	2.32	2.729 (4)	111
O15-H15AO16	0.82	1.89	2.713 (4)	179
O18-H18AO23	0.82	2.25	2.623 (5)	108
O20-H20AO21	0.82	2.59	3.185 (5)	131
O21-H21AO2	0.86	1.92	2.680 (5)	148
O21-H21BO19ⁱⁱ	0.86	2.32	3.163 (4)	165
O22-H22AO9^viii	0.86	1.86	2.713 (4)	170
O22-H22BO11	0.86	1.99	2.855 (5)	179
O23-H23AO12^v	0.86	1.80	2.637 (5)	166
O23-H23BO22^ix	0.86	1.92	2.781 (5)	174
C11-H11AO23	0.93	2.53	3.293 (7)	139
C34-H34AO20	0.93	2.40	3.265 (6)	154
C4-H4ACg6ⁱⁱ	0.93	2.81	3.571 (5)	140
C16-H16ACg8	0.93	2.91	3.737 (5)	149
Symmetry codes: (i) x-1, y, z-1; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z+1; (v) x-1, y, z; (vi) x, y+1, z; (vii) x+1, y, z; (viii) x, y-1, z; (ix) -x, -y, -z.

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2790 ).

Acknowledgements

This work was financial supported by Yuanpei University, Taiwan.

References

Bebout, D. & Pagola, S. (2009). Acta Cryst. E65, o317-o318.
Fukumoto, L. R. & Mazza, G. J. (2000). J. Agric. Food Chem. 48, 3597-3604.
Li, Z.-H. & Guo, M.-L. (2007). Acta Cryst. E63, o1167-o1168.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Okabe, N., Kyoyama, H. & Suzuki, M. (2001). Acta Cryst. E57, o764-o766.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds