2-Chloro-N-(4-chloro-3-iodo­phen­yl)-4-(methyl­sulfon­yl)benzamide

Wang, D.-C.; Song, H.; Yang, C.; Huang, W.-C.; Yao, S.

doi:10.1107/S1600536811053633

Volume 68
Part 1
Page o189
January 2012

Received 10 December 2011
Accepted 13 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.005 Å
R = 0.028
wR = 0.067
Data-to-parameter ratio = 16.6
Details

2-Chloro-N-(4-chloro-3-iodophenyl)-4-(methylsulfonyl)benzamide

Dao-Cai Wang,^a Hang Song,^a Chang Yang,^a Wen-Cai Huang ^a and Shun Yao ^a ^*

^aDepartment of Pharmaceutical and Biological Engineering, College of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China
Correspondence e-mail: cusack@scu.edu.cn

In the title compound, C₁₄H₁₀Cl₂INO₃S, the dihedral angle between the benzene rings is 52.13 (10)°. In the crystal, the components are linked by pairs of N-HO(sulfonyl) hydrogen bonds into centrosymmetric dimers.

Related literature

For background to benzamides, see: Castanedo et al. (2010); Tremblay et al. (2010); Mahindroo et al. (2010). For the preparation of the title compound, see: Robarge et al. (2009).

Experimental

Crystal data

C₁₄H₁₀Cl₂INO₃S
M_r = 470.09
Triclinic, $[P \overline 1]$
a = 8.8694 (6) Å
b = 10.3837 (8) Å
c = 10.4288 (5) Å
= 103.862 (5)°
= 96.452 (5)°
= 114.949 (7)°
V = 820.25 (9) Å³
Z = 2
Mo K radiation
= 2.41 mm^-1
T = 290 K
0.30 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.887, T_max = 1.000
6770 measured reflections
3323 independent reflections
2957 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.067
S = 1.07
3323 reflections
200 parameters
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.55 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.86	2.15	2.991 (3)	167
Symmetry code: (i) -x, -y+1, -z+3.

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: OLEX2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5034 ).

Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Castanedo, G. M., et al. (2010). Bioorg. Med. Chem. Lett. 20, 6748-6753.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Mahindroo, N., Connelly, M. C., Punchihewa, C., Yang, L., Yan, B. & Fujii, N. (2010). Bioorg. Med. Chem. 18, 4801-4811.
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Robarge, K. D., et al. (2009). Bioorg. Med. Chem. Lett. 19, 5576-5581.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tremblay, M. R., McGovern, K., Read, M. A. & Castro, A. C. (2010). Curr. Opin. Chem. Biol. 14, 428-435.

organic compounds