[Journal logo]

Volume 69 
Part 7 
Page o1090  
July 2013  

Received 6 June 2013
Accepted 7 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.095
Data-to-parameter ratio = 12.4
Details
Open access

N-[(2-Chlorophenyl)sulfonyl]-3-nitrobenzamide

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bUniversity College of Science, Tumkur University, Tumkur, India,cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and dDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 103, India
Correspondence e-mail: pasuchetan@yahoo.co.in

In the title compound, C13H9ClN2O5S, the dihedral angle between the benzene rings is 74.86 (11)°. The molecule is twisted at the S atom, with a dihedral angle of 82.53 (13)° between the sulfonyl benzene ring and the S-N-C=O segment. In the crystal, molecules are linked into inversion dimers through pairs of N-H...O hydrogen bonds, thereby forming R22(8) loops. Molecules are linked into C(7) [010] chains by weak C-H...O hydrogen bonds, and C-H...[pi] interactions are also observed.

Related literature

For similar structures, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.], 2010[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794.]); Suchetan et al. (2011[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o930.], 2012[Suchetan, P. A., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o1507.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9ClN2O5S

  • Mr = 340.73

  • Orthorhombic, P b c a

  • a = 12.290 (8) Å

  • b = 13.548 (9) Å

  • c = 17.240 (11) Å

  • V = 2870 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.44 mm-1

  • T = 298 K

  • 0.32 × 0.26 × 0.18 mm

Data collection
  • Bruker APEXII diffractometer

  • 22957 measured reflections

  • 2523 independent reflections

  • 2170 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.095

  • S = 1.06

  • 2523 reflections

  • 203 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the nitrobenzene ring.

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O2i 0.81 (2) 2.15 (2) 2.954 (3) 169 (2)
C11-H11...O3ii 0.93 2.50 3.411 (3) 166
C6-H6...Cgiii 0.93 2.72 3.550 (3) 150
Symmetry codes: (i) -x, -y, -z+1; (ii) [-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7091 ).


Acknowledgements

PAS thanks the University Grants Commission (UGC), India, for financial support under its Minor Research Project scheme.

References

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.  [CSD] [CrossRef] [IUCr Journals]
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794.  [CrossRef] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o930.  [CSD] [CrossRef] [IUCr Journals]
Suchetan, P. A., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o1507.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1090  [ doi:10.1107/S1600536813015912 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.