(E)-N′-(5-Chloro-2-hydroxy­benzyl­idene)-p-toluene­sulfonohydrazide

Reza Kia; Hoong-Kun Fun; Hadi Kargar

doi:10.1107/S1600536808038695

. 2008 Nov 22;64(Pt 12):o2424. doi: 10.1107/S1600536808038695

(E)-N′-(5-Chloro-2-hydroxybenzylidene)-p-toluenesulfonohydrazide

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

PMCID: PMC2960077 PMID: 21581392

Abstract

The title compound, C₁₄H₁₃ClN₂O₃S, features an intramolecular O—H⋯N hydrogen bond which generates an S(6) ring motif. Intermolecular N—H⋯O hydrogen bonds and C—H⋯O close contacts link neighbouring molecules forming R ₂ ²(13) ring motifs. In the crystal structure, molecules are further linked by C—H⋯Cl interactions, forming one-dimensional extended chains along the c axis. The dihedral angle between the two benzene rings is 86.06 (3)°. The crystal structure is further stabilized by weak intermolecular π–π interactions [interplanar stacking distance = 3.357 (7) Å].

Related literature

For related structures and applications, see, for example: Kayser et al. (2004 ▶); Tierney et al. (2006 ▶); Tabatabaee et al. (2007 ▶); Ali et al. (2007 ▶); Mehrabi et al. (2008 ▶); Kia et al. (2008 ▶). For the values of bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₃ClN₂O₃S
M _r = 324.78
Monoclinic,
a = 15.7454 (3) Å
b = 9.8338 (2) Å
c = 9.8455 (2) Å
β = 105.941 (1)°
V = 1465.83 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 100.0 (1) K
0.45 × 0.38 × 0.31 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.836, T _max = 0.883
16498 measured reflections
5274 independent reflections
4761 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.093
S = 1.10
5274 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038695/pk2133sup1.cif

e-64-o2424-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038695/pk2133Isup2.hkl

e-64-o2424-Isup2.hkl^{(258.3KB, 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
O1—H1O1⋯N1	0.75 (2)	2.00 (2)	2.6690 (13)	149 (2)
N2—H1N2⋯O2ⁱ	0.881 (16)	1.961 (17)	2.8375 (12)	172.8 (17)
C7—H7A⋯O1ⁱ	0.93	2.59	3.3679 (14)	142
C10—H10A⋯Cl1ⁱⁱ	0.93	2.82	3.7256 (12)	164
C12—H12A⋯O3ⁱⁱⁱ	0.93	2.48	3.3549 (14)	157

Open in a new tab

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

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. HK thanks PNU for financial support.

supplementary crystallographic information

Comment

Sulfonamides were the first class of antimicrobial agents to be discovered. Sulfonamides (sulfanilamide, sulfamethoxazole, sulfafurazole) are structural analogues of p-aminobenzoic acid (PABA) and compete with PABA to block its conversion to dihydrofolic acid (Kayser et al., 2004). 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). With regard to all of the above important features, we report the crystal structure of the title compound.

The title compund (Fig. I), is a novel sulfonamide derivative. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable with those in related structures (Kia et al., 2008; Mehrabi et al., 2008; Ali et al. 2007). An intramolecular O—H···N hydrogen bond generates S(6) ring motif, and the molecule adopts a 'vault' shape. Intermolecular N—H···O and C—H···O interactions link neighbouring molecules by R₂²(13) ring motifs. The two benzene rings make a dihedral angle of 86.06 (3)°. In the crystal structure, molecules are linked together by intermolecular C—H···Cl, N—H···O and C—H···O interactions, forming one-dimensional extended chains along the c axis. The crystal structure is further stabilized by weak intermolecular π-π interactions [interplanar distance = 3.357 (7) Å].

Experimental

The synthetic method has been described earlier (Kia et al., 2008). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution at room temperature.