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Volume 69 
Part 7 
Pages o1122-o1123  
July 2013  

Received 12 June 2013
Accepted 13 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 98 K
Mean [sigma](C-C) = 0.004 Å
R = 0.056
wR = 0.133
Data-to-parameter ratio = 12.1
Details
Open access

4-Carboxypyridin-1-ium 2,4,5-tricarboxybenzoate monohydrate

aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The title hydrated salt, C6H6NO2+·C10H5O8-·H2O, was isolated from the 1:1 cocrystallization of benzene-1,2,4,5-tetracarboxylic acid and isonicotinic acid in ethanol solution. In the crystal, the cation is close to planar [r.m.s. deviation = 0.085 Å for the nine fitted atoms; the C-C-C-O(carbonyl) torsion angle = -8.7 (4)°], but twists are evident in the anion, with all but the carboxylic acid group diagonally opposite the carboxylate group being significantly twisted out of the plane of the benzene ring [C-C-C-O(carbonyl) torsion angles = -118.1 (2), -157.6 (2), 4.3 (3) and 77.3 (3)°]. In the crystal, the ions and water molecules are consolidated into a three-dimensional architecture by O-H...O and N-H...O hydrogen bonding along with C-H...O interactions.

Related literature

For background to pharmaceutical co-crystals, see: Almarsson & Zaworotko (2004[Almarsson, Ö. & Zaworotko, M. J. (2004). Chem. Commun. pp. 1889-1896.]). For related co-crystallization studies on 1,2,4,5-benzenetetracarboxylic acid, see: Arman & Tiekink (2013a[Arman, H. D. & Tiekink, E. R. T. (2013a). J. Chem. Crystallogr. 43, 134-137.],b[Arman, H. D. & Tiekink, E. R. T. (2013b). Z. Kristallogr. Cryst. Mat. 228, doi: 10.1524/zkri.2013.1612.]). For the structure of isonicotinic acid, see: Takusagawa & Shimada (1976[Takusagawa, F. & Shimada, A. (1976). Acta Cryst. B32, 1925-1927.]). For the structure of the analogous salt formed from nicotinic acid, see: Dos Santos et al. (2012[Dos Santos, L. H. R., Rodrigues, B. L., Idemori, Y. M. & Fernandes, N. G. (2012). J. Mol. Struct. 1014, 102-109.]). For the calculation of pKa values, see: Chemaxon (2009[Chemaxon (2009). MarvinSketch. www.chemaxon.com.]).

[Scheme 1]

Experimental

Crystal data
  • C6H6NO2+·C10H5O8-·H2O

  • Mr = 395.27

  • Triclinic, [P \overline 1]

  • a = 9.724 (2) Å

  • b = 10.007 (2) Å

  • c = 10.755 (2) Å

  • [alpha] = 99.56 (1)°

  • [beta] = 114.667 (8)°

  • [gamma] = 110.283 (9)°

  • V = 830.7 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 98 K

  • 0.33 × 0.25 × 0.20 mm

Data collection
  • Rigaku AFC12/SATURN724 diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.807, Tmax = 1.000

  • 5233 measured reflections

  • 3414 independent reflections

  • 3200 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.133

  • S = 1.17

  • 3414 reflections

  • 281 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4O...O3i 0.84 (3) 1.82 (3) 2.654 (3) 176 (3)
O6-H6O...O1ii 0.85 (5) 1.69 (5) 2.534 (3) 174 (5)
O8-H8O...O1W 0.85 (5) 1.79 (5) 2.634 (3) 171 (6)
O10-H10O...O2iii 0.85 (4) 1.78 (4) 2.625 (3) 172 (4)
N1-H1N...O5iv 0.89 (4) 1.86 (4) 2.711 (3) 160 (4)
O1W-H1W...O2v 0.85 (2) 2.16 (2) 2.957 (3) 156 (3)
O1W-H2W...O2iii 0.85 (1) 2.05 (2) 2.853 (3) 158 (4)
C6-H6...O7v 0.95 2.40 3.267 (3) 151
C12-H12...O9vi 0.95 2.35 3.179 (4) 146
C14-H14...O6vii 0.95 2.40 3.300 (4) 159
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z; (iii) x, y, z-1; (iv) x-1, y, z; (v) -x+1, -y+2, -z+1; (vi) -x, -y+2, -z; (vii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005[Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7093 ).


Acknowledgements

We gratefully thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Almarsson, Ö. & Zaworotko, M. J. (2004). Chem. Commun. pp. 1889-1896.  [CrossRef]
Arman, H. D. & Tiekink, E. R. T. (2013a). J. Chem. Crystallogr. 43, 134-137.  [Web of Science] [CrossRef] [ChemPort]
Arman, H. D. & Tiekink, E. R. T. (2013b). Z. Kristallogr. Cryst. Mat. 228, doi: 10.1524/zkri.2013.1612.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chemaxon (2009). MarvinSketch. www.chemaxon.com.
Dos Santos, L. H. R., Rodrigues, B. L., Idemori, Y. M. & Fernandes, N. G. (2012). J. Mol. Struct. 1014, 102-109.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Takusagawa, F. & Shimada, A. (1976). Acta Cryst. B32, 1925-1927.  [CrossRef] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1122-o1123   [ doi:10.1107/S1600536813016437 ]

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