(IUCr) 1,4-Dihydroxyquinoxaline-2,3(1H,4H)-dione

Volume 64
Part 3
Pages o571-o572
March 2008

Received 30 January 2008
Accepted 4 February 2008
Online 8 February 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.035
wR = 0.072
Data-to-parameter ratio = 7.7
Details

1,4-Dihydroxyquinoxaline-2,3(1H,4H)-dione

Rajab Abu-El-Halawah,^a Basem Fares Ali,^a ^* Mohammad M. Ibrahim,^b Jalal A. Zahra ^c and Wolfgang Frey ^b

^aDepartment of Chemistry, Al al-Bayt University, Mafraq, Jordan,^bInstitut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany, and ^cChemistry Department, University of Jordan, Amman, Jordan
Correspondence e-mail: bfali@aabu.edu.jo

The asymmetric unit of the title compound, C₈H₆N₂O₄, contains one half-molecule; a twofold rotation axis bisects the molecule. The quinoxaline ring is planar, which can be attributed to electron delocalization. In the crystal structure, intermolecular O-HO hydrogen bonds link the molecules into R₂²(10) motifs, leading to layers, which interact via phenyl-phenyl interactions (CC distances in the range 3.238-3.521 Å).

Related literature

For general background, see: Zarranz et al. (2004); Chowdhury et al. (2004); Monge et al. (1995); Fuchs et al. (2001); Dance (1996); Bernstein et al. (1995). For related literature, see: Elina & Tsyrul'nikova (1963); Akkurt et al. (2004); Mustaphi et al. (2001); Oxtoby et al. (2005); Ley & Seng (1975); For bond-length data, see: Allen et al. (1987);

Experimental

Crystal data

C₈H₆N₂O₄
M_r = 194.15
Orthorhombic, C 222₁
a = 4.2562 (6) Å
b = 17.630 (3) Å
c = 10.4775 (17) Å
V = 786.2 (2) Å³
Z = 4
Mo K radiation
= 0.14 mm^-1
T = 294 (2) K
0.50 × 0.20 × 0.10 mm

Data collection

Nicolet P3 diffractometer
Absorption correction: none
1004 measured reflections
529 independent reflections
437 reflections with I > 2(I)
R_int = 0.022
3 standard reflections every 50 reflections intensity decay: 2%

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.071
S = 1.07
529 reflections
69 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.12 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.96 (3)	1.63 (3)	2.584 (2)	174 (3)
Symmetry code: (i) x, -y+1, -z.

Data collection: P3/PC Data Collection Software (Siemens, 1991); cell refinement: P3/PC Data Collection Software; data reduction: SHELXTL-Plus (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2425 ).

Acknowledgements

We acknowledge financial support from Al al-Bayt University (Jordan). We are grateful for a research grant from Deutsche Forschungsgemeinschaft (DFG) 2007 (to R. Abu-El-Halawa) and for the generous hospitality and discussions of Prof Volker Jäger and to Helmut Griesser at the Institute of Organic Chemistry, University of Stuttgart, Germany. We also thank Mr Raed Soudqi for his help.

References

Akkurt, M., Öztürk, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o1266-o1268.
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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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Dance, I. G. (1996). Supramolecular Inorganic Chemistry, in The Crystal as a Supramolecular Entity, edited by G. R. Desiraju, pp. 137-233. New York: John Wiley.
Elina, A. S. & Tsyrul'nikova, L. G. (1963). Zh. Obshch. Khim. 33, 1544-1551.
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Mustaphi, N. E., Ferfra, S., Essassi, E. M. & Pierrot, M. (2001). Acta Cryst. E57, o176-o177.
Oxtoby, N. S., Blake, A. J., Champness, N. R. & Wilson, C. (2005). Chem. Eur. J. 11, 4643-4654.
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Siemens (1991). P3/PC Data Collection Software. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
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Zarranz, B., Jaso, A., Aldana, I. & Monge, A. (2004). Bioorg. Med. Chem. 12, 3711-3721.

organic compounds