2-(2-Nitro­phenyl­sulfin­yl)acetonitrile

Benmebarek, S.; Boudraa, M.; Bouacida, S.; Merazig, H.

doi:10.1107/S1600536813004832

Volume 69
Part 3
Page o432
March 2013

Received 18 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.070
Data-to-parameter ratio = 18.3
Details

2-(2-Nitrophenylsulfinyl)acetonitrile

Sabrina Benmebarek,^a Mhamed Boudraa,^a Sofiane Bouacida ^a,^b ^* and Hocine Merazig ^a

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université Mentouri-Constantine, 25000 , Algeria, and ^bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, Algeria
Correspondence e-mail: Bouacida_Sofiane@yahoo.fr

In the title compound, C₈H₆N₂O₃S, the dihedral angle between the nitro group and the benzene ring is 6.76 (9)°. The bond-angle sum at the S atom is 308.1°. In the crystal, molecules are linked by C-HO hydrogen bonds to generate (010) sheets. The crystal studied was found to be a racemic twin.

Related literature

For a related structure and background to sulfoxides, see: Benmebarek et al. (2012). For related structures see: Yan (2010); Kobayashi et al. (2003).

Experimental

Crystal data

C₈H₆N₂O₃S
M_r = 210.21
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.4114 (2) Å
b = 10.7602 (4) Å
c = 15.1837 (5) Å
V = 884.11 (5) Å³
Z = 4
Mo K radiation
= 0.35 mm^-1
T = 295 K
0.26 × 0.2 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
8401 measured reflections
2348 independent reflections
2222 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.070
S = 1.05
2348 reflections
128 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.18 e Å^-3
Absolute structure: Flack (1983), 1379 Friedel pairs
Flack parameter: 0.53 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O2ⁱ	0.93	2.41	3.3198 (18)	165
C7-H7AO2ⁱⁱ	0.97	2.50	3.1190 (19)	122
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7044 ).

Acknowledgements

This work is supported by `Unité de recherche de Chimie de l'Environnement et Moléculaire Structurale' (CHEMS), Université de Constantine, Algeria. Thanks are due to MESRS and ATRST (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence thématique de recherche en sciences et technologie, Algérie) via the PNR program for financial support.

References

Benmebarek, S., Boudraa, M., Bouacida, S. & Daran, J.-C. (2012). Acta Cryst. E68, o3207.
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Kobayashi, K., Sato, A., Sakamoto, S. & Yamaguchi, K. (2003). J. Am. Chem. Soc. 125, 3035-3045.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yan, Z. (2010). Acta Cryst. E66, o3311.

organic compounds