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

Ejaz; Khan, I.U.; Sheikh, T.A.; Harrison, W.T.A.

doi:10.1107/S1600536811045326

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 (C-C) = 0.003 Å
R = 0.036
wR = 0.102
Data-to-parameter ratio = 21.1
Details

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

Ejaz,^a Islam Ullah Khan,^a ^* Tahir Ali Sheikh ^a and William T. A. Harrison ^b

^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-HO and C-HCl interactions link the molecules.

Related literature

For related structures, see: Ejaz et al. (2011a,b).

Experimental

Crystal data

C₂₄H₂₄Cl₄N₂O₄S₂
M_r = 610.37
Triclinic, $[P \overline 1]$
a = 8.0396 (2) Å
b = 11.1512 (3) Å
c = 15.5723 (3) Å
= 87.454 (1)°
= 83.378 (1)°
= 87.995 (1)°
V = 1384.77 (6) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.102
S = 1.04
6905 reflections
327 parameters
H-atom parameters constrained
_max = 0.47 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7BO3ⁱ	0.97	2.59	3.511 (2)	158
C17-H17BO1ⁱⁱ	0.97	2.58	3.516 (3)	164
C24-H24Cl1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); 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.
Ejaz, Khan, I. U., Ahmad, H., Harrison, W. T. A. & Sheikh, T. A. (2011b). Acta Cryst. E67, o3038.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds