N-Benzo­ylbenzene­sulfonamide

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

doi:10.1107/S1600536809037222

Volume 65
Part 10
Page o2516
October 2009

Received 11 September 2009
Accepted 14 September 2009
Online 26 September 2009

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.005 Å
R = 0.055
wR = 0.171
Data-to-parameter ratio = 12.7
Details

N-Benzoylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. A. Suchetan ^a 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, C₁₃H₁₁NO₃S, the conformation of the N-H bond in the C-SO₂-NH-C(O)-C segment is anti to the C=O bond. The molecule is twisted at theN atom with a dihedral angle of 86.5(1)° between the sulfonyl benzene ring and the -SO₂-NH-C=O segment. Furthermore, the dihedral angle between the two benzene rings is 80.3(1)°. The crystal structure features inversion-related dimers linked by pairs of N-HO(S) hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2008a,b; 2009).

Experimental

Crystal data

C₁₃H₁₁NO₃S
M_r = 261.29
Triclinic, $[P \overline 1]$
a = 5.8396 (7) Å
b = 10.178 (1) Å
c = 10.405 (1) Å
= 90.187 (8)°
= 99.074 (9)°
= 99.617 (9)°
V = 601.83 (11) Å³
Z = 2
Cu K radiation
= 2.40 mm^-1
T = 299 K
0.50 × 0.33 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan North et al., 1968 T_min = 0.380, T_max = 0.889
2354 measured reflections
2125 independent reflections
1962 reflections with I > 2(I)
R_int = 0.011
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.171
S = 1.18
2125 reflections
167 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.65 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.79 (3)	2.22 (3)	2.981 (4)	163 (4)
Symmetry code: (i) -x+1, -y+1, -z+2.

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: TK2540 ).

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship.

References

Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1692.
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1825.
Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o1219.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
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