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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 [sigma](C-C) = 0.005 Å
R = 0.055
wR = 0.171
Data-to-parameter ratio = 12.7
Details
Open access

N-Benzoylbenzenesulfonamide

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-H...O(S) hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2008a[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1692.],b[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1825.]; 2009[Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o1219.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11NO3S

  • Mr = 261.29

  • Triclinic, [P \overline 1]

  • a = 5.8396 (7) Å

  • b = 10.178 (1) Å

  • c = 10.405 (1) Å

  • [alpha] = 90.187 (8)°

  • [beta] = 99.074 (9)°

  • [gamma] = 99.617 (9)°

  • V = 601.83 (11) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.40 mm-1

  • T = 299 K

  • 0.50 × 0.33 × 0.05 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.] Tmin = 0.380, Tmax = 0.889

  • 2354 measured reflections

  • 2125 independent reflections

  • 1962 reflections with I > 2[sigma](I)

  • Rint = 0.011

  • 3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 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[Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [CSD] [CrossRef] [details]
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1825.  [CSD] [CrossRef] [details]
Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o1219.  [CSD] [CrossRef] [details]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.


Acta Cryst (2009). E65, o2516  [ doi:10.1107/S1600536809037222 ]

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