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Volume 70 
Part 5 
Page o549  
May 2014  

Received 22 February 2014
Accepted 8 April 2014
Online 12 April 2014

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.101
Data-to-parameter ratio = 14.2
Details
Open access

2-(Tri­methyl­aza­nium­yl)ethyl hydrogen phosphate (phospho­choline) mono­hydrate

aDepartment of Biotechnology, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan,bFunctional Ionic liquid Laboratories, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei, Japan,cJapan Science and Technology Agency (JST), Core Research for Evolutional Science and Technology (CREST), Chiyoda, Japan, and dInstrumentation Analysis Center, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan
Correspondence e-mail: ohnoh@cc.tuat.ac.jp

In the crystal structure of the title compound, C5H14NO4P·H2O, the zwitterionic phospho­choline mol­ecules are connected by an O-H...O hydrogen bond between the phosphate groups, forming a zigzag chain along the b-axis direction. The chains are further connected through O-H...O hydrogen bonds involving water mol­ecules, forming a layer parallel to (101). Three and one C-H...O inter­actions are also observed in the layer and between the layers, respectively. The conformation of the N-C-C-O backbone is gauche with a torsion angle of -75.8 (2)°

Related literature

For related structures, see: Fujita et al. (2009[Fujita, K., MacFarlane, D. R., Noguchi, K. & Ohno, H. (2009). Acta Cryst. E65, o709.]); Pearson & Pascher (1979[Pearson, R. H. & Pascher, I. (1979). Nature, 281, 499-501.]); McAlister et al. (1979[McAlister, J., Fries, D. & Sundaralingam, M. (1979). Acta Cryst. B35, 2696-2699.]).

[Scheme 1]

Experimental

Crystal data
  • C5H14NO4P·H2O

  • Mr = 201.16

  • Monoclinic, P 21 /n

  • a = 10.4304 (2) Å

  • b = 6.8873 (1) Å

  • c = 13.4992 (3) Å

  • [beta] = 105.800 (1)°

  • V = 933.11 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.59 mm-1

  • T = 193 K

  • 0.60 × 0.40 × 0.40 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.306, Tmax = 0.424

  • 16036 measured reflections

  • 1715 independent reflections

  • 1632 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.101

  • S = 1.13

  • 1715 reflections

  • 121 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2O...O4i 0.80 (3) 1.74 (3) 2.525 (2) 167 (3)
O5-H5OA...O3ii 0.77 (3) 1.99 (3) 2.764 (2) 175 (3)
O5-H5OB...O3iii 0.75 (3) 2.04 (3) 2.784 (2) 172 (3)
C2-H2A...O3iv 0.99 2.47 3.440 (2) 167
C3-H3B...O5v 0.98 2.52 3.479 (3) 167
C3-H3C...O3vi 0.98 2.51 3.388 (2) 149
C5-H5C...O4vii 0.98 2.36 3.219 (3) 146
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]; (iv) x, y+1, z; (v) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (vi) -x, -y, -z+1; (vii) -x+1, -y, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 2004[Rigaku (2004). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); program(s) used to solve structure: Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); 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.


Supporting information for this paper is available from the IUCr electronic archives (Reference: IS5344 ).


Acknowledgements

This research was supported by a Grant-in-Aid for Scientific Research to HO (No. 21225007) and KF (No. 23750120) from the Japan Society for the Promotion of Science. KF is grateful to the Funds for Development of Human Resources in Science and Technology "Supporting positive activities for female researchers", the Ministry of Education, Culture, Sports, Science and Technology, Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Fujita, K., MacFarlane, D. R., Noguchi, K. & Ohno, H. (2009). Acta Cryst. E65, o709.  [CSD] [CrossRef] [IUCr Journals]
McAlister, J., Fries, D. & Sundaralingam, M. (1979). Acta Cryst. B35, 2696-2699.  [CrossRef] [ChemPort] [IUCr Journals]
Pearson, R. H. & Pascher, I. (1979). Nature, 281, 499-501.  [CSD] [CrossRef] [ChemPort] [PubMed] [Web of Science]
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (2004). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o549  [ doi:10.1107/S160053681400779X ]

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