4-(Benzyl­ideneamino)benzene­sulfonamide

Loughrey, B.T.; Williams, M.L.; Healy, P.C.

doi:10.1107/S1600536809030256

Volume 65
Part 9
Page o2087
September 2009

Received 30 July 2009
Accepted 30 July 2009
Online 8 August 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.085
Data-to-parameter ratio = 13.8
Details

4-(Benzylideneamino)benzenesulfonamide

Bradley T. Loughrey,^a Michael L. Williams ^a and Peter C. Healy ^a ^*

^aEskitis Institute for Cell and Molecular Therapies, Griffith University, Brisbane 4111, Australia
Correspondence e-mail: p.healy@griffith.edu.au

The title compound, C₁₃H₁₂N₂O₂S, formed by Schiff base condensation of benzaldehyde with sulfanilamide, crystallizes as discrete molecular species linked by N-HN and N-HO hydrogen bonds between the sulfamide nitrogen H atoms and the azamethine N and one sulfamide O atom, respectively, forming a two-dimensional array in the bc plane. The azamethine group is rotated slightly out of the benzaldehyde benzene plane [C-C-C-N torsion angle = 8.1 (3)°], while the dihedral angle between the two benzene rings is 30.0 (1)°.

Related literature

Condensation of substituted benzaldehydes with sulfanilamide yields a diverse array of Schiff bases which display interesting enzymatic inhibition, see Supuran et al. (1996); Lin et al. (2008). For our ongoing studies on the synthesis, structures and biological activity of organometallic Cp*Ru(II) arene complexes Loughrey et al. (2008, 2009). For related structures, see Chumakov et al. (2006); Subashini et al. (2009).

Experimental

Crystal data

C₁₃H₁₂N₂O₂S
M_r = 260.32
Monoclinic, P 2₁ /c
a = 14.5206 (8) Å
b = 11.4992 (6) Å
c = 7.7846 (5) Å
= 103.287 (6)°
V = 1265.04 (13) Å³
Z = 4
Mo K radiation
= 0.25 mm^-1
T = 296 K
0.43 × 0.31 × 0.20 mm

Data collection

Oxford-Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.900, T_max = 0.952
8991 measured reflections
2253 independent reflections
1928 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.085
S = 1.05
2253 reflections
163 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H11N4ⁱ	0.86	2.14	2.9955 (18)	171
N1-H12O11ⁱⁱ	0.87	2.13	2.9845 (19)	171
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2519 ).

Acknowledgements

We acknowledge support of this work by Griffith University, the Queensland University of Technology and the Eskitis Institute for Cell and Molecular Therapies.

References

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Chumakov, Y. M., Tsapkov, V. I., Bocelli, G., Antonsyak, B. Y., Palomares-Sanches, S. A., Oritz, R. S. & Gulya, A. P. (2006). J. Struct. Chem. 47, 923-929.
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Loughrey, B. T., Williams, M. L., Poulsen, S.-A. & Healy, P. C. (2008). Acta Cryst. E64, m1568.
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
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Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Subashini, A., Hemamalini, M., Muthiah, P. T., Bocelli, G. & Cantoni, A. (2009). J. Chem. Crystallogr. 39, 112-116.
Supuran, C. T., Nicolae, A. & Popescu, A. (1996). Eur. J. Med. Chem. 31, 431-438.

organic compounds