Bis[5-oxo-4,5-dihydro-8H-2-azonia-4,8,9-trizabicyclo[4.3.0]nona-2,6,9(1)-triene] sulfate

Ravindra, N.V.; Panpalia, G.M.; Sarma, J.A.R.P.

doi:10.1107/S1600536808038026

Volume 64
Part 12
Page o2411
December 2008

Received 24 October 2008
Accepted 15 November 2008
Online 22 November 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.096
Data-to-parameter ratio = 10.0
Details

Bis[5-oxo-4,5-dihydro-8H-2-azonia-4,8,9-trizabicyclo[4.3.0]nona-2,6,9(1)-triene] sulfate

Nittala V. Ravindra,^a Gopal M. Panpalia ^a and Jagarlapudi A. R. P. Sarma ^b ^*

^aBirla Institute of Technology, Department of Pharmaceutical Sciences, Mesra, Ranchi 835 215, India, and ^bGVK Biosciences Private Limited, S-1, Phase-1 Technocrats Industrial Estate, Balanagar, Hyderabad 500 037, India
Correspondence e-mail: sarma@gvkbio.com

In the crystal structure of the title compound, 2C₅H₅N₄O⁺·SO₄^2-, N-HO hydrogen bonds assemble the molecules into a two-dimensional network structure parallel to the cb plane. The S atom of the sulfate ion lies on a special position on a twofold axis.

Related literature

For general background, see: Elion et al. (1962); Rundles et al. (1966). For related structures, see: Prusiner & Sundaralingam (1972); Gadret et al. (1974); Sheldrick & Bell (1987); Singh & Pedersen (1993).

Experimental

Crystal data

2C₅H₅N₄O⁺·SO₄^2-
M_r = 370.32
Monoclinic, C 2/c
a = 12.337 (3) Å
b = 10.054 (2) Å
c = 11.064 (2) Å
= 102.42 (3)°
V = 1340.2 (5) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 298 (2) K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
3561 measured reflections
1323 independent reflections
1252 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.096
S = 1.05
1323 reflections
132 parameters
All H-atom parameters refined
_max = 0.32 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H3O3ⁱ	0.936 (10)	1.698 (14)	2.628 (2)	173 (3)
N3-H5O2	0.819 (10)	1.957 (18)	2.753 (3)	164 (3)
N1-H1O3ⁱⁱ	0.906 (10)	1.838 (13)	2.716 (3)	163 (3)
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: 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: GW2054 ).

Acknowledgements

NVR thanks Birla Institute of Technology for financial support. NVR also thanks Prashant M. Bhatt and Professor Gautam R. Desiraju, University of Hyderabad, for help in X-ray diffraction, and Matrix Labs Ltd, Hyderabad, for a gift sample of allopurinol.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Elion, E. B., Callahan, S. W., Hitchings, G. H., Rundles, R. W. & Laszlo, J. (1962). Cancer Chemother. Rep. 16, 197-202.
Gadret, M., Goursolle, M. & Leger, J. M. (1974). Acta Cryst. B30, 1598-1602.
Prusiner, P. & Sundaralingam, M. (1972). Acta Cryst. B28, 2148-2152.
Rundles, R. W., Metz, E. N. & Silberman, H. R. (1966). Ann. Intern. Med. 64, 229-258.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sheldrick, W. S. & Bell, P. (1987). Inorg. Chim. Acta, 137, 181-188.
Singh, P. & Pedersen, L. G. (1993). Acta Cryst. C49, 1211-1215.

organic compounds

Bis[5-oxo-4,5-dihydro-8H-2-azonia-4,8,9-trizabicyclo[4.3.0]nona-2,6,9(1)-triene] sulfate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References