2,2-Dimethyl-N-(2-methyl­phenyl­sulfon­yl)propanamide

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811003400

Volume 67
Part 2
Page o536
February 2011

Received 24 January 2011
Accepted 26 January 2011
Online 29 January 2011

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 15.3
Details

2,2-Dimethyl-N-(2-methylphenylsulfonyl)propanamide

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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 title compound, C₁₂H₁₇NO₃S, the amide H atom is syn to the ortho-methyl group of the benzene ring and the C-S-N-C torsion angle is -65.39 (17)°. The crystal structure features inversion-related dimers linked by pairs of N-HO hydrogen bonds in which the acceptor O atom is bound to the S atom.

Related literature

Sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976). Their tendency and preferences for hydrogen bonding in the solid state can give rise to polymorphism, see: Yang & Guillory (1972); Adsmond & Grant (2001). For our studies on the effect of substituents on the crystal structures of this class of compounds, see: Gowda et al. (2008a,b, 2010).

Experimental

Crystal data

C₁₂H₁₇NO₃S
M_r = 255.33
Monoclinic, P 2₁ /c
a = 7.3827 (6) Å
b = 21.986 (2) Å
c = 8.6060 (8) Å
= 97.158 (9)°
V = 1386.0 (2) Å³
Z = 4
Cu K radiation
= 2.06 mm^-1
T = 299 K
0.30 × 0.25 × 0.25 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
3884 measured reflections
2472 independent reflections
2202 reflections with I > 2(I)
R_int = 0.050
3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.098
S = 1.05
2472 reflections
162 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.38 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.82 (2)	2.10 (2)	2.906 (2)	170 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

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: TK2712 ).

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.
Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o1284.
Gowda, B. T., Foro, S., Sowmya, B. P., Nirmala, P. G. & Fuess, H. (2008a). Acta Cryst. E64, o1274.
Gowda, B. T., Foro, S., Sowmya, B. P., Nirmala, P. G. & Fuess, H. (2008b). Acta Cryst. E64, o1410.
Maren, T. H. (1976). Annu. Rev. Pharmacol Toxicol. 16, 309-327.
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.
Yang, S. S. & Guillory, J. K. (1972). J. Pharm. Sci. 61, 26-40.

organic compounds