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Volume 69 
Part 4 
Page o591  
April 2013  

Received 9 March 2013
Accepted 19 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.072
wR = 0.161
Data-to-parameter ratio = 13.0
Details
Open access

Cyclohexane-1,4-dicarboxylic acid-pyridinium-4-olate (1/1)

aFacultad de Ingenieria Mochis, Universidad Autónoma de Sinaloa, Fuente Poseidón y Prol. A. Flores S/N, CP 81223, C.U. Los Mochis, Sinaloa, México, and bCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, México
Correspondence e-mail: cenriqueza@yahoo.com.mx

In the title adduct, C5H5NO·C8H12O4, the heterocycle exists in its zwitterionic form. The cyclohexane ring exhibits a chair conformation with the carboxylic acid groups in equatorial and axial orientations. In the crystal, molecules are linked through charge-assisted O-H...O-, N+-H...O- and N+-H...O hydrogen bonds, and an additional series of C-H...O contacts, giving a pleated two-dimensional hydrogen-bonded network parallel to (-204).

Related literature

For reports on supramolecular crystal engineering and potential applications of co-crystals, see: Desiraju (1995[Desiraju, G. R. (1995). Angew. Chem. Int. Ed. 34, 2311-2327.]); Simon & Bassoul (2000[Simon, J. & Bassoul, P. (2000). In Design of Molecular Materials: Supramolecular Engineering. Berlin: Wiley-VCH.]); Weyna et al. (2009[Weyna, D. R., Shattock, T., Vishweshwar, P. & Zaworotko, M. J. (2009). Cryst. Growth Des. 9, 1106-1123.]); Aakeröy et al. (2010[Aakeröy, C. B., Champness, N. R. & Janiak, C. (2010). CrystEngComm, 12, 22-43.]); Yan et al. (2012[Yan, D., Delori, A., Lloyd, G. O., Patel, B., Friscic, T., Day, G. M., Bucar, D. K., Jones, W., Lu, J., Wei, M., Evans, D. G. & Duan, X. (2012). CrystEngComm, 14, 5121-5123.]). For related structures, see: Bhogala et al. (2005[Bhogala, B. R., Basavoju, S. & Nangia, A. (2005). CrystEngComm, 7, 551-562.]); Shattock et al. (2008[Shattock, T. R., Arora, K. K., Vishweshwar, P. & Zaworotko, M. J. (2008). Cryst. Growth Des. 8, 4533-4545.]); Yu (2012[Yu, C.-H. (2012). Acta Cryst. E68, o1989.]).

[Scheme 1]

Experimental

Crystal data
  • C5H5NO·C8H12O4

  • Mr = 267.28

  • Monoclinic, P 21 /c

  • a = 11.749 (2) Å

  • b = 11.618 (2) Å

  • c = 10.8010 (19) Å

  • [beta] = 115.383 (2)°

  • V = 1332.0 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.50 × 0.43 × 0.24 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.95, Tmax = 0.98

  • 12552 measured reflections

  • 2345 independent reflections

  • 2229 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.161

  • S = 1.02

  • 2345 reflections

  • 181 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.20 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
O1-H1'...O5 0.84 1.82 2.638 (3) 165
O3-H3'...O5i 0.84 1.76 2.594 (2) 175
N1-H1...O4ii 0.84 2.29 2.921 (3) 132
N1-H1...O5iii 0.84 2.39 3.038 (3) 134
C1-H1A...O2iv 0.98 2.67 3.625 (4) 162
C11-H11...O2iii 0.93 2.62 3.420 (5) 143
C12-H12...O4ii 0.93 2.47 3.014 (4) 117
Symmetry codes: (i) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+1; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus-NT (Bruker, 2001[Bruker (2001). SAINT-Plus-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al. 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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: PK2472 ).


Acknowledgements

This work was supported financially by the Universidad Autónoma de Sinaloa (PROFAPI 2012/049).

References

Aakeröy, C. B., Champness, N. R. & Janiak, C. (2010). CrystEngComm, 12, 22-43.
Bhogala, B. R., Basavoju, S. & Nangia, A. (2005). CrystEngComm, 7, 551-562.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2000). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SAINT-Plus-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (1995). Angew. Chem. Int. Ed. 34, 2311-2327.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Shattock, T. R., Arora, K. K., Vishweshwar, P. & Zaworotko, M. J. (2008). Cryst. Growth Des. 8, 4533-4545.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Simon, J. & Bassoul, P. (2000). In Design of Molecular Materials: Supramolecular Engineering. Berlin: Wiley-VCH.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Weyna, D. R., Shattock, T., Vishweshwar, P. & Zaworotko, M. J. (2009). Cryst. Growth Des. 9, 1106-1123.  [CSD] [CrossRef] [ChemPort]
Yan, D., Delori, A., Lloyd, G. O., Patel, B., Friscic, T., Day, G. M., Bucar, D. K., Jones, W., Lu, J., Wei, M., Evans, D. G. & Duan, X. (2012). CrystEngComm, 14, 5121-5123.  [CrossRef] [ChemPort]
Yu, C.-H. (2012). Acta Cryst. E68, o1989.  [CrossRef] [details]


Acta Cryst (2013). E69, o591  [ doi:10.1107/S160053681300754X ]

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