N-(2-Meth­oxy­phen­yl)-4-methyl­benzene­sulfonamide

Khan, I.U.; Sheikh, T.A.; Arshad, M.N.

doi:10.1107/S1600536810042984

Volume 66
Part 11
Page o2976
November 2010

Received 20 October 2010
Accepted 21 October 2010
Online 30 October 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.050
wR = 0.143
Data-to-parameter ratio = 19.4
Details

N-(2-Methoxyphenyl)-4-methylbenzenesulfonamide

Islam Ullah Khan,^a ^* Tahir Ali Sheikh ^a and Muhammad Nadeem Arshad ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan
Correspondence e-mail: iukhan.gcu@gmail.com

In the title compound, C₁₄H₁₅NO₃S, the geometry around the S atom of the SO₂ group is distorted tetrahedral. The methoxy- and methyl-substituted aromatic rings are oriented at a dihedral angle of 71.39 (9)°. Intermolecular N-HO hydrogen bonds form inversion dimers, which stabilize the crystal structure.

Related literature

For the antimicrobial activity of sulfonamide compounds, see: Gao & Pederson (2005). For a related thiazine molecule, see: Arshad et al. (2010). For a related structure, see: Aziz-ur-Rehman et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₅NO₃S
M_r = 277.33
Orthorhombic, P b c a
a = 12.7395 (9) Å
b = 11.4906 (6) Å
c = 18.6968 (10) Å
V = 2736.9 (3) Å³
Z = 8
Mo K radiation
= 0.24 mm^-1
T = 296 K
0.42 × 0.33 × 0.21 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.906, T_max = 0.951
13798 measured reflections
3376 independent reflections
1313 reflections with I > 2(I)
R_int = 0.086

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.143
S = 0.91
3376 reflections
174 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.84	2.35	3.112 (3)	151
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5047 ).

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing grant for the project to strengthen the Materials Chemistry Laboratory at GC University Lahore, Pakistan.

References

Arshad, M. N., Zia-ur-Rehman, M. & Khan, I. U. (2010). Acta Cryst. E66, o1070.
Aziz-ur-Rehman, Sajjad, M. A., Akkurt, M., Sharif, S., Abbasi, M. A. & Khan, I. U. (2010). Acta Cryst. E66, o1769.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2007). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gao, J. & Pederson, J. A. (2005). Environ. Sci. Technol. 39, 9509-9516.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds