4-[(4-Meth­oxy­benzyl­idene)amino]­benzene­sulfonamide

Idemudia, O.G.; Sadimenko, A.P.; Afolayan, A.J.; Hosten, E.C.

doi:10.1107/S1600536812018818

Volume 68
Part 6
Page o1599
June 2012

Received 18 April 2012
Accepted 26 April 2012
Online 2 May 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.095
Data-to-parameter ratio = 18.6
Details

4-[(4-Methoxybenzylidene)amino]benzenesulfonamide

Omoruyi G. Idemudia,^a ^* Alexander P. Sadimenko,^a Anthony J. Afolayan ^a and Eric C. Hosten ^b

^aDepartment of Chemistry, University of Fort Hare, Private Bag X1314, Alice 5700, South Africa, and ^bDepartment of Chemistry, Nelson Mandela Metropolitan University, PO Box 77000, Port Elizabeth 6031, South Africa
Correspondence e-mail: idemudiaog@yahoo.com

The title Schiff base compound, C₁₄H₁₄N₂O₃S, is non-planar, with a dihedral angle of 24.16 (7)° between the benzene rings. In the crystal, N-HO and N-HN hydrogen bonds link the molecules into a layer parallel to (011). Intra- and interlayer C-HO interactions and [pi] - [pi] interactions [centroid-centroid distances = 3.8900 (9) and 3.9355 (8) Å] are also present.

Related literature

For general background to the applications of sulfanilamide Schiff bases, see: Gupta et al. (2003); Khalil et al. (2009); Nagpal & Singh (2004); Sharaby (2007); Wu et al. (2004).

Experimental

Crystal data

C₁₄H₁₄N₂O₃S
M_r = 290.33
Monoclinic, P 2₁ /c
a = 16.3315 (5) Å
b = 11.1597 (3) Å
c = 7.6876 (3) Å
= 100.661 (1)°
V = 1376.92 (8) Å³
Z = 4
Mo K radiation
= 0.24 mm^-1
T = 200 K
0.60 × 0.33 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.90, T_max = 0.97
10501 measured reflections
3383 independent reflections
2821 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.095
S = 1.08
3383 reflections
182 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.39 e Å^-3

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 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2541 ).

Acknowledgements

The authors thank the Department of Chemistry and Govan Mbeki Research and Development Centre (GMRDC), University of Fort Hare, for their support.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gupta, M. K., Singh, H. L., Varshney, S. & Varshney, A. K. (2003). Bioinorg. Chem. Appl. 1, 309-320.
Khalil, R. A., Jalil, A. H. & Abd-Alrazzak, A. Y. (2009). Iran. Chem. Soc. 6, 345-352.
Nagpal, P. & Singh, R. V. (2004). Appl. Organomet. Chem. 18, 221-226.
Sharaby, C. M. (2007). Spectrochim. Acta Part A, 66, 1271-1278.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Wu, C. Y., Chen, L. H., Hwang, W. S., Chen, H. S., Chen, H. S. & Hung, C. H. (2004). J. Organomet. Chem. 689, 2192-2200.

organic compounds