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Volume 69 
Part 8 
Page o1232  
August 2013  

Received 29 June 2013
Accepted 4 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.045
wR = 0.118
Data-to-parameter ratio = 13.1
Details
Open access

N-(3-Methoxybenzoyl)-2-methylbenzenesulfonamide

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 Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and dSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India
Correspondence e-mail: pasuchetan@yahoo.co.in

In the title compound, C15H15NO4S, the dihedral angle between the methyl- and methoxy-substituted benzene rings is 88.99 (12)°. An intramolecular C-H...O hydrogen bond occurs. 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 C-H...O interactions that form C(8) chains parallel to (001). Molecules are also connected through other C-H...O hydrogen bonds along the b axis, forming additional C(8) chains. Two aromatic [pi]-[pi] stacking interactions [centroid-centroid separations = 3.6150 (1) and 3.6837 (1) Å] generate a three-dimensional architecture.

Related literature

For similar structures, see: Gowda et al. (2010[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o433.]); Suchetan et al. (2010[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1024.], 2011[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o3489.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15NO4S

  • Mr = 305.34

  • Monoclinic, C 2/c

  • a = 26.713 (5) Å

  • b = 7.3717 (4) Å

  • c = 19.636 (3) Å

  • [beta] = 131.21 (3)°

  • V = 2908.7 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 293 K

  • 0.33 × 0.27 × 0.22 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 5294 measured reflections

  • 2558 independent reflections

  • 1970 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.118

  • S = 1.04

  • 2558 reflections

  • 196 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-HN1...O2i 0.80 (3) 2.15 (4) 2.929 (4) 166
C3-H3...O3ii 0.93 2.60 3.463 (3) 155
C10-H10...O2i 0.93 2.60 3.404 (3) 145
C15-H15B...O3iii 0.96 2.36 3.323 (3) 178
C6-H6...O1 0.93 2.46 2.861 (4) 106
Symmetry codes: (i) [-x, y, -z+{\script{1\over 2}}]; (ii) x, y-1, z; (iii) [x, -y+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: SJ5340 ).


Acknowledgements

The authors thank Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions. PAS and MPS thank 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. (2010). Acta Cryst. E66, o433.  [CSD] [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, o3489.  [CSD] [CrossRef] [IUCr Journals]
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1024.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1232  [ doi:10.1107/S1600536813018539 ]

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