(E)-N′-(4-Bromo­benzyl­idene)-p-toluene­sulfonohydrazide

Reza Kia; Bijan Etemadi; Hoong-Kun Fun; Hadi Kargar

doi:10.1107/S1600536809009751

. 2009 Mar 25;65(Pt 4):o821–o822. doi: 10.1107/S1600536809009751

(E)-N′-(4-Bromobenzylidene)-p-toluenesulfonohydrazide

Reza Kia ^a, Bijan Etemadi ^b, Hoong-Kun Fun ^a,^*, Hadi Kargar ^c

PMCID: PMC2968802 PMID: 21582542

Abstract

In the title compound, C₁₄H₁₃BrN₂O₂S, a novel sulfonamide derivative, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link neighbouring molecules into different dimers along the b axis, generating R ₂ ²(8) and R ₂ ²(16) ring motifs. The dihedral angle between the benzene rings is 82.39 (13)°. The crystal structure is further stabilized by intermolecular π–π stacking interactions [centroid–centroid distances = 3.867 (2)–3.9548 (8) Å].

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures and applications, see, for example: Kia et al. (2008a ▶,b ▶); Tabatabaee et al. (2007 ▶); Ali et al. (2007 ▶); Tierney et al. 2006 ▶; Krygowski et al. (1998 ▶); Mehrabi et al. (2008 ▶); Kayser et al. (2004 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₄H₁₃BrN₂O₂S
M _r = 353.23
Triclinic,
a = 5.9565 (3) Å
b = 9.4005 (3) Å
c = 12.8020 (6) Å
α = 97.153 (2)°
β = 96.350 (2)°
γ = 92.125 (1)°
V = 705.95 (5) Å³
Z = 2
Mo Kα radiation
μ = 3.06 mm⁻¹
T = 100 K
0.57 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.276, T _max = 0.819
18030 measured reflections
5040 independent reflections
4098 reflections with I > 2˘I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.106
S = 1.11
5040 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009751/rz2299sup1.cif

e-65-0o821-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009751/rz2299Isup2.hkl

e-65-0o821-Isup2.hkl^{(246.8KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.85 (4)	2.06 (4)	2.902 (3)	171 (4)
C14—H14A⋯O1ⁱⁱ	0.98	2.57	3.420 (3)	145

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. BE thanks Shiraz University for financial support. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Sulfonamides were the first class of antimicrobial agents to be discovered. They inhibit dihydropteroate synthetase in the bacterial folic acid pathway. Although their clinical role has diminished, they are still useful in certain situations, because of its efficacy and low cost (Krygowski et al., 1998). Sulfonamides (sulfanilamide, sulfamethoxazole, sulfafurazole) are structural analogues of p-aminobenzoic acid (PABA) and compete with PABA to block its conversion to dihydrofolic acid. These agents are generally used in combination with other drugs (usually sulfonamides) to prevent or treat a number of bacterial and parasitic infections (Tierney et al., 2006). Because of the above impotrtant features, we report the crystal structure of the title compound.

The title compund (Fig. 1), is a novel sulfonamide derivative. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable with the related staructures (Kia et al. 2008a,b; Mehrabi et al., 2008; Ali et al. 2007). Intermolecular N—H···O and C—H···O hydrogen bonds link neighbouring molecules by R₂²(8) and R₂²(16) ring motifs (Bernstein et al., 1995), respectively, into different dimers along the b axis. The dihedral angle between the two benzene rings is 82.39 (13)°. The crystal structure is further stabilized by intermolecular π-π stacking interactions [Cg1···Cg1ⁱⁱⁱ = 3.9319 (15) and Cg2···Cg2^iv = 3.8677 (16) Å; the perpendicular distances are 3.6548 (10) and 3.6189 (11) Å, respectively. Symmetry codes: (iii) -x, 2 - y, 1 - z; (iv) 2 - x, 1 - y, 2 - z].

Experimental

p-Tosylhydrazine (2 mmol) was added to a 50 ml refluxing ethanolic solution of 4-bromobenzaldehyde (2 mmol). The mixture was stirred for 2 h. After cooling, the colorless crystalline solid was isolated by filtration, washed with cold ethanol, and re-crystallized from ethanol.