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Volume 65 
Part 9 
Page o2109  
September 2009  

Received 16 July 2009
Accepted 31 July 2009
Online 8 August 2009

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.099
Data-to-parameter ratio = 12.6
Details
Open access

4-(2-Hydroxyethyl)anilinium 3,5-dinitrobenzoate

aSchool of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Qld 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the title compound, C8H12NO+·C7H3N2O6-, the anilinium and hydroxyl protons of the cation result in N-H...O, N-H...(O,O) and O-H...O hydrogen-bonding interactions with carboxylate O-atom acceptors, forming a two-dimensional network structure. An intermolecular C-H...O interaction is also present.

Related literature

For related structures, see: Etter & Frankenbach (1989[Etter, M. C. & Frankenbach, G. M. (1989). Chem. Mater. 1, 10-12.]); Lynch et al. (1991a[Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1991a). Aust. J. Chem. 44, 809-816.],b[Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1991b). Aust. J. Chem. 44, 1017-1022.], 1992[Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1992). Acta Cryst. C48, 1265-1267.], 1993[Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1993). Aust. J. Chem. 46, 921-927.]); Ranganathan & Pedireddi (1998[Ranganathan, A. & Pedireddi, V. R. (1998). Tetrahedron Lett. 39, 1803-1806.]); Aakeröy et al. (2003[Aakeröy, C. B., Beatty, A. M., Helfrich, B. A. & Nieuwenhuyzen, M. (2003). Cryst. Growth Des. 6, 159-165.]); Hosomi et al. (2000[Hosomi, H., Ohba, S. & Ito, Y. (2000). Acta Cryst. C56, e144-e146.]).

[Scheme 1]

Experimental

Crystal data
  • C8H12NO+·C7H3N2O6-

  • Mr = 349.30

  • Monoclinic, P 21 /n

  • a = 15.9566 (19) Å

  • b = 5.7844 (5) Å

  • c = 17.4118 (14) Å

  • [beta] = 102.811 (10)°

  • V = 1567.1 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 297 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.950, Tmax = 0.980

  • 5928 measured reflections

  • 3061 independent reflections

  • 2203 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.099

  • S = 0.98

  • 3061 reflections

  • 242 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O11A-H11A...O11i 0.89 (2) 1.88 (2) 2.7569 (16) 168 (2)
N4A-H41A...O12 0.958 (19) 1.924 (19) 2.845 (2) 160.8 (17)
N4A-H42A...O11ii 0.936 (19) 2.02 (2) 2.8905 (19) 154.0 (18)
N4A-H42A...O12ii 0.936 (19) 2.53 (2) 3.1033 (18) 119.9 (14)
N4A-H43A...O11Aiii 1.005 (19) 1.783 (19) 2.785 (2) 174.4 (19)
C5A-H5A...O11Aiv 0.93 2.43 3.317 (2) 161
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x, -y+1, -z; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis Pro (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); 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: BT5012 ).


Acknowledgements

The authors acknowledge financial support from the Australian Research Council and the School of Physical and Chemical Sciences, Queensland University of Technology.

References

Aakeröy, C. B., Beatty, A. M., Helfrich, B. A. & Nieuwenhuyzen, M. (2003). Cryst. Growth Des. 6, 159-165.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Etter, M. C. & Frankenbach, G. M. (1989). Chem. Mater. 1, 10-12.  [CrossRef] [ChemPort]
Hosomi, H., Ohba, S. & Ito, Y. (2000). Acta Cryst. C56, e144-e146.  [CrossRef] [details]
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1991a). Aust. J. Chem. 44, 809-816.  [ChemPort]
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1991b). Aust. J. Chem. 44, 1017-1022.  [ChemPort]
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1992). Acta Cryst. C48, 1265-1267.  [CrossRef] [details]
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1993). Aust. J. Chem. 46, 921-927.  [ChemPort]
Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Ranganathan, A. & Pedireddi, V. R. (1998). Tetrahedron Lett. 39, 1803-1806.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
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 (2009). E65, o2109  [ doi:10.1107/S1600536809030426 ]

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