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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 [sigma](C-C) = 0.005 Å
R = 0.028
wR = 0.067
Data-to-parameter ratio = 16.6
Details
Open access

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

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-H...O(sulfonyl) hydrogen bonds into centrosymmetric dimers.

Related literature

For background to benzamides, see: Castanedo et al. (2010[Castanedo, G. M., et al. (2010). Bioorg. Med. Chem. Lett. 20, 6748-6753.]); Tremblay et al. (2010[Tremblay, M. R., McGovern, K., Read, M. A. & Castro, A. C. (2010). Curr. Opin. Chem. Biol. 14, 428-435.]); Mahindroo et al. (2010[Mahindroo, N., Connelly, M. C., Punchihewa, C., Yang, L., Yan, B. & Fujii, N. (2010). Bioorg. Med. Chem. 18, 4801-4811.]). For the preparation of the title compound, see: Robarge et al. (2009[Robarge, K. D., et al. (2009). Bioorg. Med. Chem. Lett. 19, 5576-5581.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10Cl2INO3S

  • Mr = 470.09

  • Triclinic, [P \overline 1]

  • a = 8.8694 (6) Å

  • b = 10.3837 (8) Å

  • c = 10.4288 (5) Å

  • [alpha] = 103.862 (5)°

  • [beta] = 96.452 (5)°

  • [gamma] = 114.949 (7)°

  • V = 820.25 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.887, Tmax = 1.000

  • 6770 measured reflections

  • 3323 independent reflections

  • 2957 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.067

  • S = 1.07

  • 3323 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2006[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.]); 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.  [CrossRef] [ChemPort] [PubMed]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Mahindroo, N., Connelly, M. C., Punchihewa, C., Yang, L., Yan, B. & Fujii, N. (2010). Bioorg. Med. Chem. 18, 4801-4811.  [CrossRef] [ChemPort] [PubMed]
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Robarge, K. D., et al. (2009). Bioorg. Med. Chem. Lett. 19, 5576-5581.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tremblay, M. R., McGovern, K., Read, M. A. & Castro, A. C. (2010). Curr. Opin. Chem. Biol. 14, 428-435.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o189  [ doi:10.1107/S1600536811053633 ]

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