[Journal logo]

Volume 69 
Part 6 
Page o832  
June 2013  

Received 24 April 2013
Accepted 27 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.104
Data-to-parameter ratio = 15.0
Details
Open access

2-Chloro-6-(2,3-dichlorobenzenesulfonamido)benzoic acid

aDepartment of Chemistry, Materials Chemistry Laboratory, GC University, Lahore 54000, Pakistan,bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cCenter of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia
Correspondence e-mail: malikg781@yahoo.com, mnachemist@hotmail.com

In the title compound, C13H8Cl3NO4S, the aromatic rings are oriented at a dihedral angle of 68.94 (1)° and the molecule adopts a V-shape. An intramolecular N-H...O interaction generates a six-membered S(6) ring motif. In the crystal, pairs of O-H...O hydrogen bonds involving the carboxy group link the molecules into inversion dimers with an R22(8) motif. N-H...O and non-classical C-H...O interactions connect the molecules, forming sheets propagating in (100).

Related literature

For the synthesis, see: Arshad et al. (2012[Arshad, M. N., Danish, M., Tahir, M. N., Aabideen, Z. U. & Asiri, A. M. (2012). Acta Cryst. E68, o2665.]) For related structures, see: Arshad et al. (2009[Arshad, M. N., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Shafiq, M. (2009). Acta Cryst. E65, o281.], 2011[Arshad, M. N., Khan, I. U., Rafique, H. M., Asiri, A. M. & Shafiq, M. (2011). Acta Cryst. E67, o1327.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8Cl3NO4S

  • Mr = 380.61

  • Monoclinic, P 21 /c

  • a = 9.0164 (3) Å

  • b = 18.6017 (5) Å

  • c = 9.8574 (3) Å

  • [beta] = 111.653 (3)°

  • V = 1536.62 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 6.83 mm-1

  • T = 296 K

  • 0.38 × 0.20 × 0.18 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.467, Tmax = 1.000

  • 11742 measured reflections

  • 3018 independent reflections

  • 2597 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.104

  • S = 1.04

  • 3018 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.60 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3 0.86 2.55 2.940 (2) 108
C12-H12...O3i 0.93 2.59 3.425 (3) 150
O3-H3...O4ii 0.82 1.85 2.666 (2) 176
N1-H1...O2iii 0.86 2.30 3.128 (2) 162
C5-H5...O4iv 0.93 2.53 3.256 (4) 135
C10-H10...O1v 0.93 2.51 3.165 (3) 127
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+2; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z+1; (v) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5312 ).


Acknowledgements

The authors would like to thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via the Research Group Track of Grant No. (3-102/428).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Arshad, M. N., Danish, M., Tahir, M. N., Aabideen, Z. U. & Asiri, A. M. (2012). Acta Cryst. E68, o2665.  [CSD] [CrossRef] [details]
Arshad, M. N., Khan, I. U., Rafique, H. M., Asiri, A. M. & Shafiq, M. (2011). Acta Cryst. E67, o1327.  [CSD] [CrossRef] [details]
Arshad, M. N., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Shafiq, M. (2009). Acta Cryst. E65, o281.  [CSD] [CrossRef] [details]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o832  [ doi:10.1107/S1600536813011574 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.