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Volume 64 
Part 8 
Page o1387  
August 2008  

Received 19 June 2008
Accepted 27 June 2008
Online 5 July 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.010 Å
R = 0.072
wR = 0.205
Data-to-parameter ratio = 19.6
Details
Open access

2-Iodo-N-(2-nitrophenylsulfanyl)aniline

aDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile,bDepartamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, and cInstituto de Bio-Orgánica 'Antonio González', Universidad de La Laguna, Astrofísico Francisco Sánchez N°2, La Laguna, Tenerife, Spain
Correspondence e-mail: ivanbritob@yahoo.com

In title compound, C12H9IN2O2S, the nitro group is rotated slightly, by 8.91 (3)°, out of the plane of the aromatic ring to which it is bonded. Between the two aromatic rings the CSN plane is at a dihedral angle of 84.0 (7)° to the HNC plane. Molecules are linked by C-H...O interactions into a double helical supramolecular architecture. There are no iodo-nitro, [pi]-[pi] or C-H...[pi](arene) interactions.

Related literature

For related literature, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Brito et al. (2004[Brito, I., Vargas, D., León, Y., Cárdenas, A., López-Rodríguez, M. & Wittke, O. (2004). Acta Cryst. E60, o1668-o1670.], 2005[Brito, I., Vargas, D., Reyes, A., Cárdenas, A. & López-Rodríguez, M. (2005). Acta Cryst. C61, o234-o236.], 2006[Brito, I., López-Rodríguez, M., Vargas, D. & León, Y. (2006). Acta Cryst. E62, o914-o916.]); Glidewell et al. (2003[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o95-o97.]); Kuhle (1973[Kuhle, E. (1973). The Chemistry of the Sulfenic Acids, pp. 60-74. Stuttgart: G. Thieme.]); Pauling (1960[Pauling, L. (1960). The Nature of the Chemical Bond, 3rd ed., pp. 257-264. Ithaca: Cornell University Press.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9IN2O2S

  • Mr = 372.17

  • Trigonal, [R \overline 3]

  • a = 28.6221 (12) Å

  • c = 8.4062 (17) Å

  • V = 5963.9 (13) Å3

  • Z = 18

  • Mo K[alpha] radiation

  • [mu] = 2.57 mm-1

  • T = 298 (2) K

  • 0.47 × 0.32 × 0.20 mm

Data collection
  • Nonius KappaCCD area-detector diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.380, Tmax = 0.600

  • 11358 measured reflections

  • 3251 independent reflections

  • 2801 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.205

  • S = 1.21

  • 3251 reflections

  • 166 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.04 e Å-3

  • [Delta][rho]min = -1.05 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10...O1i 0.93 2.55 3.445 (10) 161
Symmetry code: (i) [-y+{\script{2\over 3}}, x-y-{\script{2\over 3}}, z-{\script{2\over 3}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York; Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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 PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); 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: FL2204 ).


Acknowledgements

This work was supported by a grant from the Universidad de Antofagasta (DI-1324-06). We thank the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the CSD system. AM and AR thank the Universidad de Antofagasta for PhD fellowships.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Brito, I., López-Rodríguez, M., Vargas, D. & León, Y. (2006). Acta Cryst. E62, o914-o916.
Brito, I., Vargas, D., León, Y., Cárdenas, A., López-Rodríguez, M. & Wittke, O. (2004). Acta Cryst. E60, o1668-o1670.
Brito, I., Vargas, D., Reyes, A., Cárdenas, A. & López-Rodríguez, M. (2005). Acta Cryst. C61, o234-o236.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o95-o97.  [CrossRef] [details]
Kuhle, E. (1973). The Chemistry of the Sulfenic Acids, pp. 60-74. Stuttgart: G. Thieme.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York; Academic Press.
Pauling, L. (1960). The Nature of the Chemical Bond, 3rd ed., pp. 257-264. Ithaca: Cornell University Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2008). E64, o1387  [ doi:10.1107/S1600536808019491 ]

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