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

Brito, I.; Cárdenas, A.; Mundaca, A.; López-Rodríguez, M.; Reyes, A.

doi:10.1107/S1600536808019491

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 (C-C) = 0.010 Å
R = 0.072
wR = 0.205
Data-to-parameter ratio = 19.6
Details

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

Iván Brito,^a ^* Alejandro Cárdenas,^b Aldo Mundaca,^a Matías López-Rodríguez ^c and Andrea Reyes ^a

^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-HO 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); Brito et al. (2004, 2005, 2006); Glidewell et al. (2003); Kuhle (1973); Pauling (1960).

Experimental

Crystal data

C₁₂H₉IN₂O₂S
M_r = 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 radiation
= 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) T_min = 0.380, T_max = 0.600
11358 measured reflections
3251 independent reflections
2801 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.072
wR(F²) = 0.205
S = 1.21
3251 reflections
166 parameters
H-atom parameters constrained
_max = 1.04 e Å^-3
_min = -1.05 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10O1ⁱ	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); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

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

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organic compounds