N-Benzoyl-4-nitro­benzene­sulfonamide monohydrate

Suchetan, P.A.; Foro, S.; Gowda, B.T.; Vidya, V.M.

doi:10.1107/S1600536811051439

Volume 68
Part 1
Page o10
January 2012

Received 28 November 2011
Accepted 29 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.056
wR = 0.110
Data-to-parameter ratio = 12.5
Details

N-Benzoyl-4-nitrobenzenesulfonamide monohydrate

P. A. Suchetan,^a Sabine Foro,^b B. Thimme Gowda ^a ^* and V. M. Vidya ^c

^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, C₁₃H₁₀N₂O₅S·H₂O, the dihedral angle between the sulfonyl and benzoyl benzene rings is 83.4 (1)°. In the crystal, the water molecule forms four hydrogen bonds with three different molecules of N-benzoyl-4-nitrobenzenesulfonamide. One of the H atoms of H₂O forms a bifurcated hydrogen bond with a sulfonyl and the carbonyl O atoms. Molecules are linked into a three-dimensional network by N-HO and O-HO 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), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substituted-benzoyl)-arylsulfonamides, see: Suchetan et al. (2011) and on N-chloroarylamides, see: Gowda et al. (1996).

Experimental

Crystal data

C₁₃H₁₀N₂O₅S·H₂O
M_r = 324.31
Monoclinic, P 2₁ /c
a = 22.687 (2) Å
b = 5.0673 (4) Å
c = 12.755 (1) Å
= 100.04 (1)°
V = 1443.9 (2) Å³
Z = 4
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.46 × 0.08 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.891, T_max = 0.985
4828 measured reflections
2608 independent reflections
2039 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.110
S = 1.26
2608 reflections
208 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO6	0.86 (2)	1.92 (2)	2.763 (4)	170 (3)
O6-H61O2ⁱ	0.84 (2)	2.14 (2)	2.935 (4)	158 (4)
O6-H62O3ⁱⁱ	0.82 (2)	2.23 (3)	2.919 (4)	142 (4)
O6-H62O1ⁱⁱ	0.82 (2)	2.33 (3)	2.988 (3)	138 (4)
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5737 ).

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.
Gowda, B. T., Jyothi, K., Kozisek, J. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 656-660.
Gowda, B. T., Svoboda, I. & Fuess, H. (2004). Z. Naturforsch. Teil A, 59, 845-852.
Jayalakshmi, K. L. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 491-500.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suchetan, P. A., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o3515.

organic compounds