4-Methyl-N-(4-nitro­benzo­yl)benzene­sulfonamide

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

doi:10.1107/S1600536811009470

Volume 67
Part 4
Page o917
April 2011

Received 4 March 2011
Accepted 12 March 2011
Online 19 March 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R = 0.051
wR = 0.128
Data-to-parameter ratio = 11.2
Details

4-Methyl-N-(4-nitrobenzoyl)benzenesulfonamide

P. A. Suchetan,^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 title compound, C₁₄H₁₂N₂O₅S, the dihedral angle between the sulfonyl benzene ring and the -SO₂-NH-C-O segment is 81.5 (2)° and that between the sulfonyl and the benzoyl benzene rings is 89.8 (1)°. In the crystal, molecules are linked into chains along the b axis via intermolecular N-HO hydrogen bonds. C-HO interactions are also observed.

Related literature

For background to our study of the effect of substituents on the structures of methanesulfonamides, see: Gowda et al. (2007). For the effect of substituents on the structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2005). For the effect of substituents on the structures of N-(p-substituted benzoyl)-p-substituted benzenesulfonamides, see: Suchetan et al. (2010a,b).

Experimental

Crystal data

C₁₄H₁₂N₂O₅S
M_r = 320.32
Monoclinic, P 2₁
a = 11.722 (3) Å
b = 5.137 (1) Å
c = 12.488 (3) Å
= 105.09 (2)°
V = 726.0 (3) Å³
Z = 2
Mo K radiation
= 0.25 mm^-1
T = 293 K
0.40 × 0.12 × 0.08 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 = 0.907, T_max = 0.980
2664 measured reflections
2265 independent reflections
1993 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.128
S = 1.17
2265 reflections
203 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.36 e Å^-3
Absolute structure: Flack (1983), 605 Friedel pairs
Flack parameter: -0.05 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.85 (3)	2.22 (3)	3.054 (4)	164 (4)
N1-H1NO1ⁱⁱ	0.85 (3)	2.54 (4)	2.944 (5)	110 (3)
C9-H9O3ⁱⁱⁱ	0.93	2.58	3.254 (5)	130
C13-H13O2ⁱ	0.93	2.53	3.347 (5)	147
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) x, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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: VM2084 ).

Acknowledgements

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

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2339.
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.
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. (2010a). Acta Cryst. E66, o327.
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1510.

organic compounds