2-Amino-1,3-benzothia­zol-3-ium dihydrogen phosphate

Siddiqui, S.Z.; Waqas, U.; Akkurt, M.; Aziz-ur-Rehman; Khan, I.U.

doi:10.1107/S1600536810025547

Volume 66
Part 8
Page o1929
August 2010

Received 27 June 2010
Accepted 29 June 2010
Online 7 July 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.038
wR = 0.096
Data-to-parameter ratio = 16.5
Details

2-Amino-1,3-benzothiazol-3-ium dihydrogen phosphate

Sabahat Zahra Siddiqui,^a Usama Waqas,^a Mehmet Akkurt,^b ^* Aziz-ur-Rehman ^a and Islam Ullah Khan ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

The cation of the title compound, C₇H₇N₂S⁺·H₂PO₄^-, is almost planar (r.m.s deviation = 0.017 Å for all non-H atoms). In the crystal structure, the cations and anions are connected by N-HO and O-HO hydrogen bonds, with [pi] - [pi] stacking interactions between neighbouring 1,3-thiazole and benzene rings [centroid-centroid distance = 3.5711 (11) Å], forming a three-dimensional network.

Related literature

For the structural parameters of some organic dihydrogenomonophosphates, see: Gholivand et al. (2007); Mrad et al. (2009). For the biological and pharmacological properties of heterocyclic compounds, see: Malik et al. (2010); Sinha & Tiwari (1986). For the synthesis, see: Thomas et al. (2003).

Experimental

Crystal data

C₇H₇N₂S⁺·H₂PO₄^-
M_r = 248.20
Monoclinic, P 2₁ /c
a = 12.3915 (4) Å
b = 10.1572 (3) Å
c = 8.3159 (2) Å
= 103.775 (1)°
V = 1016.56 (5) Å³
Z = 4
Mo K radiation
= 0.47 mm^-1
T = 296 K
0.25 × 0.09 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
9333 measured reflections
2490 independent reflections
1938 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.096
S = 1.03
2490 reflections
151 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.873 (16)	1.800 (16)	2.6693 (18)	174 (3)
N2-H6O3ⁱⁱ	0.86 (2)	2.39 (2)	3.138 (2)	147 (2)
N2-H6O4ⁱⁱ	0.86 (2)	2.31 (2)	3.076 (2)	149.3 (19)
N2-H7O3ⁱ	0.862 (18)	2.018 (18)	2.875 (2)	172 (2)
O1-H8O2ⁱⁱⁱ	0.809 (19)	1.795 (19)	2.6017 (18)	175 (3)
O4-H9O3^iv	0.801 (17)	1.765 (17)	2.5654 (18)	178 (3)
Symmetry codes: (i) x, y-1, z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (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: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5282 ).

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gholivand, K., Zare, K., Afshar, F., Shariatinia, Z. & Khavasi, H. R. (2007). Acta Cryst. E63, o4027.
Malik, J. K., Manvi, F. V., Nanjwede, B. K., Singh, S. & Purohit, P. (2010). Pharm. Lett. 2, 347-359.
Mrad, M. L., Akriche, S., Rzaigui, M. & Ben Nasr, C. (2009). Acta Cryst. E65, o757-o758.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sinha, A. I. P. & Tiwari, S. P. (1986). Curr. Sci. 55, 386-390.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Thomas, L., Gupta, A. & Gupta, V. (2003). J. Fluorine Chem. 22, 207-213.

organic compounds