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Volume 68 
Part 1 
Page o46  
January 2012  

Received 29 November 2011
Accepted 1 December 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.010 Å
R = 0.105
wR = 0.185
Data-to-parameter ratio = 13.4
Details
Open access

4-Chloro-N-(3-methylbenzoyl)benzenesulfonamide monohydrate

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India,bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and cDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 102, India
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C14H12ClNO3S·H2O, the dihedral angle between the sulfonyl and benzoyl benzene rings is 84.4 (2)°. In the crystal, every water molecule forms four hydrogen bonds with three different molecules of 4-chloro-N-(3-methylbenzoyl)benzenesulfonamide. One of the water H atoms forms a bifurcated hydrogen bond with both the sulfonyl and the carbonyl O atoms of the same molecule. Molecules are linked into layers in the ab plane through N-H...O and O-H...O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2004[Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 59, 845-852.]), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004[Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.]), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Kozisek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656-660.]), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2011[Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o22.]) and on N-chloroarylamides, see: Gowda et al. (1996[Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO3S·H2O

  • Mr = 327.77

  • Orthorhombic, P b c a

  • a = 5.0148 (6) Å

  • b = 12.864 (2) Å

  • c = 46.314 (5) Å

  • V = 2987.7 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.41 mm-1

  • T = 293 K

  • 0.46 × 0.14 × 0.06 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.834, Tmax = 0.976

  • 5972 measured reflections

  • 2684 independent reflections

  • 1959 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.105

  • wR(F2) = 0.185

  • S = 1.35

  • 2684 reflections

  • 200 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O4 0.86 (2) 1.93 (2) 2.771 (8) 169 (6)
O4-H41...O1i 0.84 (2) 2.29 (7) 2.916 (7) 131 (8)
O4-H41...O3i 0.84 (2) 2.42 (6) 3.117 (8) 140 (8)
O4-H42...O2ii 0.84 (2) 2.35 (6) 3.022 (8) 137 (8)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: BT5739 ).


Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty.

References

Gowda, B. T., Dou, S. Q. & Weiss, A. (1996). Z. Naturforsch. Teil A, 51, 627-636.  [ChemPort]
Gowda, B. T., Jyothi, K., Kozisek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656-660.  [ChemPort]
Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 59, 845-852.  [ChemPort]
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.  [ChemPort]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o22.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o46  [ doi:10.1107/S1600536811051932 ]

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