2-Ureido-1,3-thia­zol-3-ium dihydrogen phosphate

Gubina, K.; Shatrava, I.; Ovchynnikov, V.; Amirkhanov, V.

doi:10.1107/S1600536811021337

Volume 67
Part 7
Page o1607
July 2011

Received 24 May 2011
Accepted 2 June 2011
Online 11 June 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 14.9
Details

2-Ureido-1,3-thiazol-3-ium dihydrogen phosphate

Kateryna Gubina,^a ^* Iuliia Shatrava,^a Vladimir Ovchynnikov ^a and Vladimir Amirkhanov ^a

^aNational Taras Shevchenko University, Department of Chemistry, Volodymyrska Street 64, 01033 Kyiv, Ukraine
Correspondence e-mail: katlig@univ.kiev.ua

The title compound, C₄H₆N₃OS⁺·H₂PO₄^-, (I), was obtained as a result of hydrolysis of [(1,3-thiazol-2-ylamino)carbonyl]phosphoramidic acid, (II), in water. X-ray analysis has shown that the N-P bond in (II) breaks, leading to the formation of the substituted carbamide (I). This compound exists as an internal salt. The unit cell consists of a urea cation and an anion of H₂PO₄^-. Protonation of the N atom of the heterocyclic ring was confirmed by the location of the H atom in a difference Fourier map. The molecules of substituted urea are connected by OO hydrogen bonds into unlimited planes. In turn, those planes are connected to each other via N-HO hydrogen bonds with molecules of phosphoric acid, forming a three-dimensional polymer.

Related literature

For background to the chemistry of phosphorus-organic compounds, see: Ly & Woollins (1998). For details of the synthesis and properties of the [(1,3-thiazol-2-ylamino)carbonyl]phosphoramidic acid, see: Kirsanov & Levchenko (1957); Smaliy et al.(2003). For structural analogues of phosphorylated carbacylamides and their properties, see: Amirkhanov et al. (1997). For a structural investigation of phosphortriamidic compounds, see: Ovchynnikov et al. (1997). For the synthesis of the aminothiazol-containing phosphortriamides, see: Shatrava et al. (2009). For a description of the attractive interaction in thiazole compounds, see: Burling & Goldstein (1992); Angyan et al. (1987).

Experimental

Crystal data

C₄H₆N₃OS⁺·H₂PO₄^-
M_r = 241.16
Monoclinic, P 2₁ /c
a = 11.9038 (11) Å
b = 9.7936 (10) Å
c = 8.1914 (12) Å
= 97.231 (9)°
V = 947.37 (19) Å³
Z = 4
Mo K radiation
= 0.51 mm^-1
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 1999) T_min = 0.861, T_max = 0.904
2644 measured reflections
2239 independent reflections
1893 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.109
S = 1.05
2239 reflections
150 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.58 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O2	0.86	1.93	2.697 (2)	148
N3-H3O3	0.80 (3)	1.91 (3)	2.710 (2)	174 (3)
N1-H1AO1ⁱ	0.87 (3)	2.09 (3)	2.898 (2)	155 (2)
N1-H1BO5ⁱⁱ	0.82 (3)	2.20 (3)	3.007 (2)	170 (3)
O5-H5O2ⁱⁱⁱ	0.81 (4)	1.77 (4)	2.546 (2)	162 (4)
O4-H4O3^iv	0.80 (4)	1.82 (4)	2.613 (2)	170 (4)
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART-NT (Bruker, 1999); cell refinement: SAINT-NT (Bruker, 1999); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP within SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2693 ).

References

Amirkhanov, V. M., Ovchynnikov, V. A., Glowiak, T. & Kozlowski, H. (1997). Z. Naturforsh. Teil B, 52, 1331-1336.
Angyan, J. G., Poirier, R. A., Kucsman, A. & Csizmadia, I. G. (1987). J. Am. Chem. Soc. 109, 2237-2245.
Bruker (1999). SMART-NT, SAINT-Plus-NT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burling, F. T. & Goldstein, B. M. (1992). J. Am. Chem. Soc. 114, 2313-2320.
Kirsanov, A. & Levchenko, V. (1957). Zh. Obshch. Khim. 27, 2313-2320.
Ly, T. Q. & Woollins, J. D. (1998). Coord. Chem. Rev. 176, 451-481.
Ovchynnikov, V. A., Amirkhanov, V. M., Timoshenko, T. P., Glowiak, T. & Kozlowski, H. (1997). Z. Naturforsh. Teil B, 53, 481-484.
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