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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 [sigma](C-C) = 0.007 Å
R = 0.099
wR = 0.221
Data-to-parameter ratio = 11.9
Details
Open access

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

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-H...O and O-H...O hydrogen bonding and weak C-H...O 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[Bebout, D. & Pagola, S. (2009). Acta Cryst. E65, o317-o318.]); Li & Guo (2007[Li, Z.-H. & Guo, M.-L. (2007). Acta Cryst. E63, o1167-o1168.]); Okabe et al. (2001[Okabe, N., Kyoyama, H. & Suzuki, M. (2001). Acta Cryst. E57, o764-o766.]). For the biological activity of gallic acid (3,4,5-trihydroxybenzoic acid) and its derivatives, see: Fukumoto & Mazza (2000[Fukumoto, L. R. & Mazza, G. J. (2000). J. Agric. Food Chem. 48, 3597-3604.]).

[Scheme 1]

Experimental

Crystal data
  • C12H14N22+·2C7H5O5-·1.5H2O

  • Mr = 551.50

  • Triclinic, [P \overline 1]

  • a = 9.4445 (19) Å

  • b = 15.331 (3) Å

  • c = 18.307 (4) Å

  • [alpha] = 109.88 (3)°

  • [beta] = 93.68 (3)°

  • [gamma] = 92.90 (3)°

  • V = 2480.2 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[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.]) Tmin = 0.928, Tmax = 1.016

  • 26683 measured reflections

  • 8520 independent reflections

  • 5004 reflections with I > 2[sigma](I)

  • Rint = 0.104

Refinement
  • R[F2 > 2[sigma](F2)] = 0.099

  • wR(F2) = 0.221

  • S = 1.35

  • 8520 reflections

  • 713 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
N1-H1A...O13i 0.86 1.98 2.793 (5) 158
N1-H1A...O14i 0.86 2.32 2.914 (5) 127
N2-H2A...O11 0.86 1.74 2.571 (5) 163
N2-H2A...O12 0.86 2.60 3.297 (5) 139
N3-H3B...O1ii 0.86 1.67 2.514 (5) 166
N4-H4C...O3iii 0.86 1.97 2.804 (5) 165
N4-H4C...O4iii 0.86 2.47 3.026 (5) 123
O3-H3A...O7 0.82 1.83 2.652 (4) 175
O4-H4B...O16iv 0.82 2.06 2.804 (4) 151
O5-H5B...O6v 0.82 1.81 2.634 (5) 180
O8-H8A...O21 0.82 1.90 2.715 (4) 175
O9-H9B...O15vi 0.82 2.47 3.153 (4) 141
O10-H10B...O15vi 0.82 2.12 2.812 (5) 142
O13-H13A...O17vii 0.82 1.75 2.569 (4) 172
O14-H14A...O15 0.82 2.32 2.729 (4) 111
O15-H15A...O16 0.82 1.89 2.713 (4) 179
O18-H18A...O23 0.82 2.25 2.623 (5) 108
O20-H20A...O21 0.82 2.59 3.185 (5) 131
O21-H21A...O2 0.86 1.92 2.680 (5) 148
O21-H21B...O19ii 0.86 2.32 3.163 (4) 165
O22-H22A...O9viii 0.86 1.86 2.713 (4) 170
O22-H22B...O11 0.86 1.99 2.855 (5) 179
O23-H23A...O12v 0.86 1.80 2.637 (5) 166
O23-H23B...O22ix 0.86 1.92 2.781 (5) 174
C11-H11A...O23 0.93 2.53 3.293 (7) 139
C34-H34A...O20 0.93 2.40 3.265 (6) 154
C4-H4A...Cg6ii 0.93 2.81 3.571 (5) 140
C16-H16A...Cg8 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[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: DENZO (Otwinowski & Minor, 1997[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.]) and SCALEPACK; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [CSD] [CrossRef] [details]
Fukumoto, L. R. & Mazza, G. J. (2000). J. Agric. Food Chem. 48, 3597-3604.  [ISI] [CrossRef] [PubMed] [ChemPort]
Li, Z.-H. & Guo, M.-L. (2007). Acta Cryst. E63, o1167-o1168.  [CrossRef] [details]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Okabe, N., Kyoyama, H. & Suzuki, M. (2001). Acta Cryst. E57, o764-o766.  [CSD] [CrossRef] [details]
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.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2010). E66, o2056-o2057   [ doi:10.1107/S1600536810027169 ]

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