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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 [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.070
Data-to-parameter ratio = 18.3
Details
Open access

2-(2-Nitrophenylsulfinyl)acetonitrile

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-H...O 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[Benmebarek, S., Boudraa, M., Bouacida, S. & Daran, J.-C. (2012). Acta Cryst. E68, o3207.]). For related structures see: Yan (2010[Yan, Z. (2010). Acta Cryst. E66, o3311.]); Kobayashi et al. (2003[Kobayashi, K., Sato, A., Sakamoto, S. & Yamaguchi, K. (2003). J. Am. Chem. Soc. 125, 3035-3045.]).

[Scheme 1]

Experimental

Crystal data
  • C8H6N2O3S

  • Mr = 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[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.070

  • S = 1.05

  • 2348 reflections

  • 128 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1379 Friedel pairs

  • Flack parameter: 0.53 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O2i 0.93 2.41 3.3198 (18) 165
C7-H7A...O2ii 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[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR2002 (Burla et al., 2005[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Kobayashi, K., Sato, A., Sakamoto, S. & Yamaguchi, K. (2003). J. Am. Chem. Soc. 125, 3035-3045.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yan, Z. (2010). Acta Cryst. E66, o3311.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o432  [ doi:10.1107/S1600536813004832 ]

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