3,4-Bis(4-nitro­phen­yl)-1,2,5-oxadiazole 2-oxide

Alhouari, G.; Kerbal, A.; Larbi, N.B.; Hadda, T.B.; Daoudi, M.; Stoeckli-Evans, H.

doi:10.1107/S1600536807066640

Volume 64
Part 2
Page o511
February 2008

Received 20 November 2007
Accepted 12 December 2007
Online 23 January 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.060
wR = 0.133
Data-to-parameter ratio = 16.2
Details

3,4-Bis(4-nitrophenyl)-1,2,5-oxadiazole 2-oxide

Ghali Alhouari,^a Abdelali Kerbal,^a Najib Ben Larbi,^a Taibi Ben Hadda,^b ^* Maria Daoudi ^b and Helen Stoeckli-Evans ^c

^aLaboratoire de Chimie Organique, Faculté des Sciences Dhar El Mehraz, Fès, Morocco,^bLaboratoire d'Activation Moléculaire, Faculté des Sciences, 60000 Oujda, Morocco, and ^cInstitut de Microtechnique, Université de Neuchâtel, Rue Emile Argand 11, CH-2009 Neuchâtel, Switzerland
Correspondence e-mail: tbenhadda@yahoo.fr

The title compound, C₁₄H₈N₄O₆, a new 1,2,5-oxadiazole N-oxide derivative, was formed by dimerization of 4-nitrobenzaldehyde oxime. The compound crystallizes with two independent molecules per asymmetric unit. The N-oxide O atom is disordered over two sites in each molecule; site occupancy factors are 0.57/0.43 and 0.5/0.5. The mean planes through the two benzene rings are inclined to the planar 1,2,3-oxadiazole ring by 25.03 (11) and 41.64 (11)° in one molecule, and 22.58 (11) and 42.66 (11)° in the other molecule, the smaller angle being for the ring on the oxide side of the oxadiazole ring in each case. In the crystal structure, the individual molecules form centrosymmetric dimers linked via C-HO hydrogen bonds. The dimers of one molecule are then linked to those of the other molecule via C-HO hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature, see: Sillitoe & Harding (1978); Easton et al. (1995); Baker et al. (2002); Allen (2002); Allen et al. (1987); Howe & Shelton (1990); Kerbal et al. (1990); Smietana et al. (1999).

Experimental

Crystal data

C₁₄H₈N₄O₆
M_r = 328.24
Monoclinic, P 2₁ /c
a = 17.3977 (11) Å
b = 7.2813 (4) Å
c = 21.5341 (13) Å
= 91.667 (5)°
V = 2726.7 (3) Å³
Z = 8
Mo K radiation
= 0.13 mm^-1
T = 173 (2) K
0.40 × 0.35 × 0.30 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: none
29047 measured reflections
7339 independent reflections
5558 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.133
S = 1.15
7339 reflections
452 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O5ⁱ	0.95	2.59	3.283 (3)	130
C14-H14O23ⁱⁱ	0.95	2.46	3.244 (3)	139
C25-H25O25ⁱⁱⁱ	0.95	2.57	3.358 (3)	141
C27-H27O1A^iv	0.95	2.36	3.254 (4)	156
C31-H31O5^v	0.95	2.52	3.261 (3)	135
C34-H34O4ⁱⁱ	0.95	2.50	3.284 (3)	140
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z; (iv) x+1, y, z; (v) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2154 ).

Acknowledgements

This work was supported by the Ministry of Education of the Kingdom of Morocco (Projet Globale de Recherche of the Université Mohamed Premier, grant PGR-BH-2005).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
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.
Baker, K. W. J., March, A. R., Parsons, S., Paton, R. M. & Stewart, G. W. (2002). Tetrahedron, 58, 8505-8513.
Easton, C. J., Hughes, C. M., Tiekink, E. R. T., Savage, G. P. & Simpson, G. W. (1995). Z. Kristallogr. 210, 625-626.
Howe, R. K. & Shelton, B. R. (1990). J. Org. Chem. 55, 4603-4607.
Kerbal, A., Tshiamala, K., Cerutti, E., Laude, B. & Vebrel, J. (1990). Bull. Soc. Chim. Fr. 127, 252-257.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sillitoe, A. K. & Harding, M. M. (1978). Acta Cryst. B34, 2021-2022.
Smietana, M., Gouverneur, V. & Mioskowski, C. (1999). Tetrahedron Lett. 40, 1291-1294.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Stoe & Cie (2006). X-AREA (Version 1.35) and X-RED32 (Version 1.31). Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds