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

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536809030426

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 (C-C) = 0.002 Å
R = 0.037
wR = 0.099
Data-to-parameter ratio = 12.6
Details

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

Graham Smith ^a ^* and Urs D. Wermuth ^a

^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-HO, N-H(O,O) and O-HO hydrogen-bonding interactions with carboxylate O-atom acceptors, forming a two-dimensional network structure. An intermolecular C-HO interaction is also present.

Related literature

For related structures, see: Etter & Frankenbach (1989); Lynch et al. (1991a,b, 1992, 1993); Ranganathan & Pedireddi (1998); Aakeröy et al. (2003); Hosomi et al. (2000).

Experimental

Crystal data

C₈H₁₂NO⁺·C₇H₃N₂O₆^-
M_r = 349.30
Monoclinic, P 2₁ /n
a = 15.9566 (19) Å
b = 5.7844 (5) Å
c = 17.4118 (14) Å
= 102.811 (10)°
V = 1567.1 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.950, T_max = 0.980
5928 measured reflections
3061 independent reflections
2203 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(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
_max = 0.21 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O11A-H11AO11ⁱ	0.89 (2)	1.88 (2)	2.7569 (16)	168 (2)
N4A-H41AO12	0.958 (19)	1.924 (19)	2.845 (2)	160.8 (17)
N4A-H42AO11ⁱⁱ	0.936 (19)	2.02 (2)	2.8905 (19)	154.0 (18)
N4A-H42AO12ⁱⁱ	0.936 (19)	2.53 (2)	3.1033 (18)	119.9 (14)
N4A-H43AO11Aⁱⁱⁱ	1.005 (19)	1.783 (19)	2.785 (2)	174.4 (19)
C5A-H5AO11A^iv	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); 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: 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.
Etter, M. C. & Frankenbach, G. M. (1989). Chem. Mater. 1, 10-12.
Hosomi, H., Ohba, S. & Ito, Y. (2000). Acta Cryst. C56, e144-e146.
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1991a). Aust. J. Chem. 44, 809-816.
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1991b). Aust. J. Chem. 44, 1017-1022.
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1992). Acta Cryst. C48, 1265-1267.
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1993). Aust. J. Chem. 46, 921-927.
Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Ranganathan, A. & Pedireddi, V. R. (1998). Tetrahedron Lett. 39, 1803-1806.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds