Ammonium hydrogen (RS)-[(5-methyl-2-oxo-1,3-oxazolidin-3-yl)meth­yl]phospho­nate

Todorov, P.; Naydenova, E.; Nikolova, R.P.; Shivachev, B.L.

doi:10.1107/S1600536809050338

Volume 66
Part 1
Page o6
January 2010

Received 16 November 2009
Accepted 23 November 2009
Online 4 December 2009

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (O-C) = 0.003 Å
Disorder in main residue
R = 0.035
wR = 0.097
Data-to-parameter ratio = 11.7
Details

Ammonium hydrogen (RS)-[(5-methyl-2-oxo-1,3-oxazolidin-3-yl)methyl]phosphonate

Petar Todorov,^a Emilia Naydenova,^a Rositsa P. Nikolova ^b and Boris L. Shivachev ^b ^*

^aUniversity of Chemical Technology and Metallurgy, Department of Organic Chemistry, 8 Kl. Ohridski Boulevard, 1756 Sofia, Bulgaria, and ^bCentral Laboratory of Mineralogy and Crystallography, Bulgarian Academy of Sciences, Acad G. Bonchev Str. build. 107, 1113 Sofia, Bulgaria
Correspondence e-mail: blshivachev@gmail.com

In the title compound, NH₄⁺·C₅H₉NO₅P^-, the five-membered methyloxazolidin-2-one unit is disordered over two positions, the major component having a site occupancy of 0.832 (9). A three-dimensional network of O-HO and N-HO hydrogen bonds stabilizes the crystal structure.

Related literature

For general background of the use of phosphonic and aminophosphonic acids as chelating agents in metal extraction and as medicinal compounds, see: Metlushka et al. (2009); Naydenova et al. (2009); Matczak-Jon & Videnova-Adrabinska (2005). For related structures, see: Dudko et al. (2009); Shivachev et al. (2005); Todorov et al. (2006); Ying et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

NH₄⁺·C₅H₉NO₅P^-
M_r = 212.14
Triclinic, $[P \overline 1]$
a = 6.471 (3) Å
b = 8.801 (3) Å
c = 9.427 (4) Å
= 70.76 (2)°
= 70.658 (18)°
= 89.363 (16)°
V = 475.4 (3) Å³
Z = 2
Mo K radiation
= 0.29 mm^-1
T = 290 K
0.30 × 0.28 × 0.21 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: none
3673 measured reflections
1855 independent reflections
1606 reflections with I > 2(I)
R_int = 0.027
3 standard reflections frequency: 120 min intensity decay: -1%

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.097
S = 1.05
1855 reflections
159 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-HN1O1	0.85	1.94	2.789 (2)	177
O2-H1AO3ⁱ	1.07	1.53	2.5770 (19)	166
N2-HN2O1ⁱⁱ	0.86	1.93	2.772 (2)	165
N2-HN3O3ⁱⁱⁱ	0.89	1.93	2.793 (2)	161
N2-HN4O4^iv	0.97	1.88	2.827 (2)	167
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2491 ).

Acknowledgements

This work was supported by the University of Chemical Metallurgy and Technology (project 10646).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Dudko, A., Bon, V., Kozachkova, A. & Pekhnyo, V. (2009). Acta Cryst. E65, o1961.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Matczak-Jon, E. & Videnova-Adrabinska, V. (2005). Coord. Chem. Rev. 249, 2458-2488.
Metlushka, K. E., Kashemirov, B. A., Zheltukhin, V. F., Sadkova, D. N., Buchner, B., Hess, C., Kataeva, O. N., McKenna, C. N. & Alfonsov, V. A. (2009). Chem. Eur. J. 15, 6718-6722.
Naydenova, E. D., Todorov, P. T. & Troev, K. D. (2009). Amino Acids. In the press, doi: 10.1007/s00726-009-0254-7.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shivachev, B., Petrova, R., Kossev, K. & Troev, K. (2005). Acta Cryst. E61, o134-o136.
Todorov, P., Naydenova, E., Petrova, R., Shivachev, B. & Troev, K. (2006). Acta Cryst. C62, o661-o662.
Ying, S.-M., Lin, J.-Y., Zhou, G.-P., Luo, Q.-Y. & Wu, J.-H. (2007). Acta Cryst. E63, o1153-o1154.

organic compounds