4-[(4-Meth­oxy­benzyl­idene)amino]­benzene­sulfonamide

Omoruyi G Idemudia; Alexander P Sadimenko; Anthony J Afolayan; Eric C Hosten

doi:10.1107/S1600536812018818

. 2012 May 2;68(Pt 6):o1599. doi: 10.1107/S1600536812018818

4-[(4-Methoxybenzylidene)amino]benzenesulfonamide

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

PMCID: PMC3379209 PMID: 22719407

Abstract

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—H⋯O and N—H⋯N hydrogen bonds link the molecules into a layer parallel to (011). Intra- and interlayer C—H⋯O interactions and π–π 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 ▶). graphic file with name e-68-o1599-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₄N₂O₃S
M _r = 290.33
Monoclinic,
a = 16.3315 (5) Å
b = 11.1597 (3) Å
c = 7.6876 (3) Å
β = 100.661 (1)°
V = 1376.92 (8) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.095
S = 1.08
3383 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018818/hy2541sup1.cif

e-68-o1599-sup1.cif^{(23KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018818/hy2541Isup2.hkl

e-68-o1599-Isup2.hkl^{(165.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018818/hy2541Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812018818/hy2541Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

Biological applications of sulfa compounds either alone or as metal complexes are well known (Gupta et al., 2003; Nagpal & Singh, 2004). Their chelating powers towards metal ions tend to increase on forming a Schiff base by way of reaction with a carbonyl (Khalil et al., 2009; Sharaby, 2007; Wu et al., 2004). Herein, we report a new sulfanilamide Schiff base (Fig. 1), as part of our look at developing better chelating ligands from biologically active amine compounds.

The least-squares planes through the phenyl rings of the benzenesulfonamide and methoxybenzaldehyde groups have a dihedral angle of 24.16 (7)°. In the crystal, the molecules are stacked along the c axis and linked by N—H···O and N—H···N hydrogen bonds (Table 1 and Fig. 2) into a layer parallel to (0 1 1) (Fig. 3). The least-squares planes through adjacent two methoxybenzaldehyde phenyl rings (C11–C16) are almost parallel with a dihedral angle of 3.97° and a centroid-to-centroid distance of 3.8900 (9) Å. The centroid-to-centroid distance between adjacent two benzenesulfonamide phenyl rings (C21–C26) is 3.9355 (8) Å. C22—H22···π interaction occurs with the adjacent C21–C26 ring (H···Cg distance = 2.81 Å). Intra- and interlayer C—H···O interactions are also observed.

Experimental

A mixture of (4-aminobenzenesulfonamide)sulfadiazine and 4-methoxybenzaldehyde (anisaldehyde) (molar ratio 1:1) in methanol was refluxed for 15 h. The resultant pale yellow precipitate was isolated by filtration and recrystalized from methanol. Yield 68% and melting point 199–201°C. Single crystals suitable for X-ray analysis were obtained from methanol by slow evaporation at room temperature.