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Volume 68 
Part 11 
Page o3207  
November 2012  

Received 13 October 2012
Accepted 20 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.002 Å
R = 0.026
wR = 0.071
Data-to-parameter ratio = 18.4
Details
Open access

1-Chloromethylsulfinyl-2-nitrobenzene

aUnité de Recherche de Chimie de l'Environnement et Moléculaire, Structurale (CHEMS), Université Mentouri-Constantine, 25000 Algeria,bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, Algeria, and cLaboratoire de Chimie de Coordination, UPR CNRS 8241, 205 route de Narbonne, 31077 Toulouse Cedex, France
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the title compound, C7H6ClNO3S, the nitro group forms a dihedral angle of 2.7 (4)° with the benzene ring. The bond-angle sum at the S atom is 303.7°. In the crystal, molecules are linked by weak C-H...O hydrogen bonds, forming layers lying parallel to (-101).

Related literature

For the biological and pharmacological activity of sulfoxides, see, for example: Melzig et al. (2009[Melzig, L., Rauhut, C. B. & Knochel, P. (2009). Chem. Commun. pp. 3536-3538.]); Huang et al. (2010[Huang, J.-Y., Li, S.-J. & Wang, Y.-G. (2010). J. Carbohydr. Chem. 29, 142-153.]). 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
  • C7H6ClNO3S

  • Mr = 219.65

  • Monoclinic, P 21 /c

  • a = 12.2394 (5) Å

  • b = 5.5009 (2) Å

  • c = 14.5537 (11) Å

  • [beta] = 116.631 (4)°

  • V = 875.92 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.65 mm-1

  • T = 180 K

  • 0.23 × 0.20 × 0.18 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.900, Tmax = 1.000

  • 10209 measured reflections

  • 2172 independent reflections

  • 1799 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.071

  • S = 1.05

  • 2172 reflections

  • 118 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O12i 0.95 2.44 3.384 (2) 173
C7-H7A...O1ii 0.99 2.36 3.2478 (18) 149
C7-H7B...O1iii 0.99 2.50 3.332 (2) 142
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6974 ).


Acknowledgements

This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université Mentouri-Constantine, Algeria. Thanks are due to MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique and ANDRU (l'Agence Nationale pour le Développement de la Recherche Universitaire) for financial support via the PNR programm.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
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. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Huang, J.-Y., Li, S.-J. & Wang, Y.-G. (2010). J. Carbohydr. Chem. 29, 142-153.  [ISI] [CrossRef]
Kobayashi, K., Sato, A., Sakamoto, S. & Yamaguchi, K. (2003). J. Am. Chem. Soc. 125, 3035-3045.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Melzig, L., Rauhut, C. B. & Knochel, P. (2009). Chem. Commun. pp. 3536-3538.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yan, Z. (2010). Acta Cryst. E66, o3311.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3207  [ doi:10.1107/S1600536812043553 ]

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