N-(3,5-Dichloro­phen­yl)-2,4-dimethyl­benzene­sulfonamide

Nirmala, P.G.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536810013504

Volume 66
Part 5
Page o1090
May 2010

Received 1 April 2010
Accepted 12 April 2010
Online 17 April 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.005 Å
R = 0.053
wR = 0.189
Data-to-parameter ratio = 14.4
Details

N-(3,5-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide

P. G. Nirmala,^a B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

In the crystal structure of the title compound, C₁₄H₁₃Cl₂NO₂S, the conformation of the N-C bond in the C-SO₂-NH-C segment has gauche torsions with respect to the S=O bonds. The molecule is bent at the N atom, with an C-SO₂-NH-C torsion angle of -54.9 (3)°. The two benzene rings are tilted relative to each other by 82.3 (2)°. The molecules are linked into centrosymmetric R₂²(8) motifs by N-HO hydrogen bonds and C-H [pi] interactions along [100].

Related literature

For the preparation of the compound, see: Savitha & Gowda (2006). For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008, 2009a,b). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₃Cl₂NO₂S
M_r = 330.21
Monoclinic, C 2/c
a = 23.085 (3) Å
b = 8.113 (2) Å
c = 16.503 (3) Å
= 102.03 (2)°
V = 3022.9 (10) Å³
Z = 8
Cu K radiation
= 5.16 mm^-1
T = 299 K
0.55 × 0.45 × 0.38 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.164, T_max = 0.245
7561 measured reflections
2690 independent reflections
2340 reflections with I > 2(I)
R_int = 0.089
3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.189
S = 1.14
2690 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.56 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.86 (4)	2.05 (5)	2.900 (4)	168 (4)
C10-H10Cg1ⁱⁱ	0.93	2.92	3.834 (4)	168
Symmetry codes: (i) -x+1, -y, -z; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2275 ).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o2190.
Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o576.
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2009b). Acta Cryst. E65, o3275.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.
Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600-606.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds