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Volume 68 
Part 1 
Page o15  
January 2012  

Received 25 October 2011
Accepted 28 October 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.102
Data-to-parameter ratio = 21.1
Details
Open access

2,2',5,5'-Tetrachloro-N,N'-diethyl-N,N'-[benzene-1,3-diylbis(methylene)]dibenzenesulfonamide

aMaterials Chemistry Laboratry, Department of Chemistry, GC University, Lahore 54000, Pakistan, and bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
Correspondence e-mail: iuklodhi@yahoo.com

In the title compound, C24H24Cl4N2O4S2, the dihedral angles between the central benzene ring and the pendant rings are 58.09 (10) and 62.59 (10)°. The dihedral angle between the pendant rings is 81.64 (9)°. Both sulfonamide groups lie to the same side of the central ring but the C-S-N-C torsion angles [73.09 (16) and -117.35 (14)] and S-N-C-C torsion angles [-143.80 (14) and -111.45 (16)°] differ significantly for the two pendant chains. The N atoms are close to planar (bond angle sums = 356.4 and 359.5°). In the crystal, weak C-H...O and C-H...Cl interactions link the molecules.

Related literature

For related structures, see: Ejaz et al. (2011a[Ejaz, Khan, I. U., Ahmad, H. & Harrison, W. T. A. (2011a). Acta Cryst. E67, o3037.],b[Ejaz, Khan, I. U., Ahmad, H., Harrison, W. T. A. & Sheikh, T. A. (2011b). Acta Cryst. E67, o3038.]).

[Scheme 1]

Experimental

Crystal data
  • C24H24Cl4N2O4S2

  • Mr = 610.37

  • Triclinic, [P \overline 1]

  • a = 8.0396 (2) Å

  • b = 11.1512 (3) Å

  • c = 15.5723 (3) Å

  • [alpha] = 87.454 (1)°

  • [beta] = 83.378 (1)°

  • [gamma] = 87.995 (1)°

  • V = 1384.77 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.61 mm-1

  • T = 296 K

  • 0.50 × 0.35 × 0.30 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 25271 measured reflections

  • 6905 independent reflections

  • 5380 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.102

  • S = 1.04

  • 6905 reflections

  • 327 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7B...O3i 0.97 2.59 3.511 (2) 158
C17-H17B...O1ii 0.97 2.58 3.516 (3) 164
C24-H24...Cl1ii 0.93 2.83 3.738 (2) 166
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2337 ).


Acknowledgements

IUK thanks the Higher Education Commission of Pakistan for its financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ejaz, Khan, I. U., Ahmad, H. & Harrison, W. T. A. (2011a). Acta Cryst. E67, o3037.  [CSD] [CrossRef] [details]
Ejaz, Khan, I. U., Ahmad, H., Harrison, W. T. A. & Sheikh, T. A. (2011b). Acta Cryst. E67, o3038.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o15  [ doi:10.1107/S1600536811045326 ]

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