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Volume 69 
Part 8 
Page o1215  
August 2013  

Received 30 June 2013
Accepted 2 July 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 13.3
Details
Open access

2-Chloro-N-(3-methoxybenzoyl)benzenesulfonamide

aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,cUniversity College of Science, Tumkur University, Tumkur, India,dSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India, and eDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C14H12ClNO4S, the dihedral angle between the chloro- and methoxy-substituted benzene rings is 87.40 (1)°. In the crystal, adjacent molecules form inversion-related dimers through strong N-H...O hydrogen bonds, generating R22(8) loops. The dimers are further connected through two C-H...O interactions that form C(11) chains and R22(14) loops. Aromatic [pi]-[pi] stacking interactions [centroid-centroid separation = 3.8574 (1) Å] are also observed.

Related literature

For a similar structure, see: Gowda et al. (2010[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794.])

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO4S

  • Mr = 325.76

  • Triclinic, [P \overline 1]

  • a = 7.5731 (5) Å

  • b = 10.1861 (5) Å

  • c = 10.3636 (6) Å

  • [alpha] = 94.945 (4)°

  • [beta] = 96.581 (5)°

  • [gamma] = 110.974 (5)°

  • V = 734.56 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 293 K

  • 0.35 × 0.28 × 0.22 mm

Data collection
  • Bruker APEXII diffractometer

  • 11351 measured reflections

  • 2584 independent reflections

  • 2133 reflections with I > 2[sigma](I)

  • Rint = 0.038

  • 2 standard reflections every 1 reflections intensity decay: 10%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.101

  • S = 1.05

  • 2584 reflections

  • 195 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-HN1...O1i 0.78 (3) 2.14 (3) 2.926 (3) 170 (3)
C5-H5...O3ii 0.93 2.53 3.417 (3) 160
C3-H3...O3iii 0.93 2.60 3.338 (3) 137
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, 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: HG5328 ).


Acknowledgements

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

References

Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
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]


Acta Cryst (2013). E69, o1215  [ doi:10.1107/S1600536813018291 ]

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