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Volume 69 
Part 8 
Page o1263  
August 2013  

Received 30 June 2013
Accepted 10 July 2013
Online 17 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.112
Data-to-parameter ratio = 13.3
Details
Open access

N-(3-Methoxybenzoyl)-4-methylbenzenesulfonamide

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

In the title compound, C15H15NO4S, the dihedral angle between the benzene rings is 88.87 (1)°. In the crystal, adjacent molecules form inversion dimers through pairs of strong N-H...O hydrogen bonds, generating R22(8) loops. Two C-H...[pi] interactions and an aromatic [pi]-[pi] interaction [centroid-centroid separation = 3.8191 (1) Å] are also observed.

Related literature

For a similar structure, see: Suchetan et al. (2010[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1039.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15NO4S

  • Mr = 305.34

  • Triclinic, [P \overline 1]

  • a = 9.2474 (7) Å

  • b = 9.6660 (6) Å

  • c = 9.8764 (8) Å

  • [alpha] = 70.268 (6)°

  • [beta] = 64.052 (8)°

  • [gamma] = 86.231 (5)°

  • V = 743.69 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 293 K

  • 0.35 × 0.28 × 0.22 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.925, Tmax = 0.950

  • 11424 measured reflections

  • 2610 independent reflections

  • 2212 reflections with I > 2[sigma](I)

  • Rint = 0.037

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

  • wR(F2) = 0.112

  • S = 1.06

  • 2610 reflections

  • 196 parameters

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the sulfonyl-bound and carbonyl-bound benzene rings respectively.

D-H...A D-H H...A D...A D-H...A
N1-HN1...O1i 0.79 (2) 2.14 (2) 2.920 (2) 170 (2)
C15-H15B...Cg1ii 0.96 2.77 3.576 (3) 141
C7-H7A...Cg2iii 0.96 2.94 3.753 (3) 143
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x, -y+2, -z+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: BG2511 ).


Acknowledgements

PAS acknowledges 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.
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., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1039.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1263  [ doi:10.1107/S1600536813019107 ]

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