N-(3,5-Dimethyl­phen­yl)-4-nitro­benzene­sulfonamide

Chaithanya, U.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812047502

Volume 68
Part 12
Page o3425
December 2012

Received 17 November 2012
Accepted 19 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.039
wR = 0.074
Data-to-parameter ratio = 9.5
Details

N-(3,5-Dimethylphenyl)-4-nitrobenzenesulfonamide

U. Chaithanya,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

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

There are two independent molecules in the asymmetric unit of the title compound, C₁₄H₁₄N₂O₄S, in which the dihedral angles between the benzene rings are 56.22 (15) and 58.16 (14)°. In the crystal, N-HO_nitro hydrogen bonds link the molecules into zigzag chains running along the a-axis direction.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994); Shahwar et al. (2012), of N-arylsulfonamides, see: Chaithanya et al. (2012) and of N-chloroarylsulfonamides, see: Shetty & Gowda (2004). For hydrogen-bonding patterns and motifs, see: Adsmond & Grant (2001).

Experimental

Crystal data

C₁₄H₁₄N₂O₄S
M_r = 306.33
Orthorhombic, P n a 2₁
a = 14.708 (1) Å
b = 7.9410 (7) Å
c = 24.741 (2) Å
V = 2889.7 (4) Å³
Z = 8
Mo K radiation
= 0.24 mm^-1
T = 293 K
0.38 × 0.30 × 0.24 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 = 0.914, T_max = 0.944
6693 measured reflections
3714 independent reflections
2624 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.074
S = 1.00
3714 reflections
390 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.18 e Å^-3
Absolute structure: Flack (1983), 1005 Friedel pairs
Flack parameter: 0.04 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.85 (2)	2.35 (2)	3.129 (5)	152 (3)
N3-H3NO8ⁱⁱ	0.84 (2)	2.40 (2)	3.168 (5)	152 (3)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: BT6865 ).

Acknowledgements

UC thanks Mangalore University for the award of a research fellowship. 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

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.
Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o2823.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds