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Volume 65 
Part 4 
Page o709  
April 2009  

Received 24 February 2009
Accepted 27 February 2009
Online 6 March 2009

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Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.121
Data-to-parameter ratio = 13.8
Details
Open access

Choline dihydrogen phosphate

Kyoko Fujita,a Douglas R MacFarlane,b Keiichi Noguchic and Hiroyuki Ohnoa*

aDepartment of Biotechnology, Tokyo University of Agriculture & Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan,bSchool of Chemistry, Monash University, Wellington Road, Clayton, VIC 3800, Australia, and cInstrumentaion Analysis Center, Tokyo University of Agriculture & Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan
Correspondence e-mail: ohnoh@cc.tuat.ac.jp

In the cystal structure of the title compound, (2-hydroxyethyl)trimethylammonium dihydrogen phosphate, C5H14NO+·H2PO4-, two anions create dimeric structures via two O-H...O hydrogen bonds. The hydrogen-bonded dimers are connected by another O-H...O hydrogen bond with the hydroxyl groups of the cations, constructing a columner structure along the a axis. A number of C-H...O interactions are also present.

Related literature

For background to ionic liquids, see: Byrne et al. (2007[Byrne, N., Wang, L.-M., Belieres, J.-P. & Angell, C. A. (2007). Chem. Commun. pp. 2714-2716.]); Fujita et al. (2005[Fujita, K., MacFarlane, D. R. & Forsyth, M. (2005). Chem. Commun. pp. 4804-4806.]); Ohno (2005[Ohno, H. (2005). Electrochemical Aspects of Ionic Liquids. New York: Wiley-Interscience.]); van Rantwijk et al. (2003[Rantwijk, F. van, Madeira, L. R. & Sheldon, R. A. (2003). Trends Biotechnol. 21, 131-138.]); Seddon (1997[Seddon, K. R. (1997). J. Chem. Technol. Biotechnol. 68, 351-356.]); Wasserscheid & Welton (2002[Wasserscheid, P. & Welton, T. (2002). Ionic liquids in synthesis. Weinheim: Wiley-VCH, Verlag.]); Welton (1999[Welton, T. (1999). Chem. Rev. 99, 2071-2084.]); Zhao et al. (2008[Zhao, H., Baker, G. A., Song, Z., Olubajo, O., Crittle, T. & Peters, D. (2008). Green Chem. 10, 696-705.]).

[Scheme 1]

Experimental

Crystal data

  • C5H14NO+·H2PO4-

  • Mr = 201.16

  • Triclinic, [P \overline 1]

  • a = 6.9232 (3) Å

  • b = 8.2807 (4) Å

  • c = 9.2333 (3) Å

  • [alpha] = 84.458 (3)°

  • [beta] = 71.414 (3)°

  • [gamma] = 70.758 (3)°

  • V = 473.68 (4) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.55 mm-1

  • T = 193 K

  • 0.60 × 0.10 × 0.02 mm
Data collection

  • Rigaku RAXIS-RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.429, Tmax = 0.950

  • 8717 measured reflections

  • 1714 independent reflections

  • 1344 reflections with I > 2[sigma](I)

  • Rint = 0.053
Refinement

  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.121

  • S = 1.12

  • 1714 reflections

  • 124 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3O...O5i 0.80 (4) 1.79 (4) 2.586 (3) 178 (3)
O4-H4O...O2i 0.93 (4) 1.60 (4) 2.526 (2) 173 (3)
O5-H5O...O1ii 0.93 (4) 1.63 (4) 2.556 (3) 176 (4)
C3-H3B...O1 0.98 2.48 3.439 (3) 166
C4-H4B...O3iii 0.98 2.54 3.504 (3) 170
C4-H4C...O1iv 0.98 2.49 3.457 (3) 168
C5-H5A...O3iv 0.98 2.46 3.430 (3) 172
C5-H5B...O1iii 0.98 2.42 3.382 (3) 169
C5-H5C...O2 0.98 2.60 3.549 (3) 164
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) -x+1, -y+1, -z+1; (iv) x, y-1, z.

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson (1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2730 ).

Acknowledgements

This study was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan. KF thanks the Japan Society for the Promotion of Science (Research Fellowship for Young Scientists) for support.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Byrne, N., Wang, L.-M., Belieres, J.-P. & Angell, C. A. (2007). Chem. Commun. pp. 2714-2716.  [CrossRef]
Fujita, K., MacFarlane, D. R. & Forsyth, M. (2005). Chem. Commun. pp. 4804-4806.  [CrossRef]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Ohno, H. (2005). Electrochemical Aspects of Ionic Liquids. New York: Wiley-Interscience.
Rantwijk, F. van, Madeira, L. R. & Sheldon, R. A. (2003). Trends Biotechnol. 21, 131-138.  [ISI] [PubMed]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Seddon, K. R. (1997). J. Chem. Technol. Biotechnol. 68, 351-356.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wasserscheid, P. & Welton, T. (2002). Ionic liquids in synthesis. Weinheim: Wiley-VCH, Verlag.
Welton, T. (1999). Chem. Rev. 99, 2071-2084.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zhao, H., Baker, G. A., Song, Z., Olubajo, O., Crittle, T. & Peters, D. (2008). Green Chem. 10, 696-705.  [ISI] [CrossRef] [ChemPort]

Acta Cryst (2009). E65, o709  [ doi:10.1107/S1600536809007259 ]

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