N-(4-Methyl­benzo­yl)benzene­sulfonamide

Suchetan, P.A.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536810023974

Volume 66
Part 7
Page o1772
July 2010

Received 18 June 2010
Accepted 20 June 2010
Online 26 June 2010

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 15.0
Details

N-(4-Methylbenzoyl)benzenesulfonamide

P. A. Suchetan,^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 title compound, C₁₄H₁₃NO₃S, the conformation of the N-H bond in the C-SO₂-NH-C(O) segment is anti to the C=O bond. The dihedral angle between the sulfonyl benzene ring and the S-N-C-O segment (r.m.s. deviation = 0.039 Å) is 77.1 (1)° and that between the sulfonyl and benzoyl benzene rings is 71.9 (1)°.

Related literature

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for related structures, see: Gowda et al. (2009); Suchetan et al. (2009, 2010).

Experimental

Crystal data

C₁₄H₁₃NO₃S
M_r = 275.31
Triclinic, $[P \overline 1]$
a = 5.5519 (6) Å
b = 10.541 (1) Å
c = 11.105 (1) Å
= 85.654 (9)°
= 83.667 (9)°
= 81.949 (9)°
V = 638.36 (11) Å³
Z = 2
Mo K radiation
= 0.26 mm^-1
T = 299 K
0.40 × 0.32 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.904, T_max = 0.960
4293 measured reflections
2595 independent reflections
2207 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.109
S = 1.08
2595 reflections
173 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.30 e Å^-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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: CI5108 ).

Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

References

Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3156.
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1039.

organic compounds