(E)-N′-(4-Chloro­benzyl­idene)-p-toluene­sulfonohydrazide 0.15-hydrate

Reza Kia; Hoong-Kun Fun; Hadi Kargar

doi:10.1107/S1600536809014512

. 2009 Apr 25;65(Pt 5):o1119–o1120. doi: 10.1107/S1600536809014512

(E)-N′-(4-Chlorobenzylidene)-p-toluenesulfonohydrazide 0.15-hydrate

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

PMCID: PMC2977795 PMID: 21583931

Abstract

The asymmetric unit of the title compound, C₁₄H₁₃ClN₂O₂S·0.15H₂O, a novel sulfonamide derivative, comprises two crystallographically independent molecules (A and B) and a water molecule of crystallization, which is partially occupied. One of the molecules (B) is disordered over two positions (B and C) with refined site occupancies of 0.605 (10) and 0.395 (10). The dihedral angles between the two benzene rings in molecules A, B and C are 67.8 (3), 74.6 (5) and 84.96 (11)°, respectively. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the components of the asymmetric unit. The crystal structure is further stabilized by intermolecular π–π interactions [centroid–centroid distances = 3.4518 (10)–3.5859 (10) 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 ▶); Mehrabi et al. (2008 ▶); Tabatabaee et al. (2007 ▶); Ali et al. (2007 ▶); Tierney et al. (2006 ▶); Krygowski et al. (1998 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For related literature on bioactivity, see: Kayser et al. (2004 ▶).

Experimental

Crystal data

C₁₄H₁₃ClN₂O₂S·0.15H₂O
M _r = 311.61
Triclinic,
a = 7.9408 (2) Å
b = 11.0592 (2) Å
c = 17.7759 (4) Å
α = 77.521 (1)°
β = 83.415 (1)°
γ = 70.313 (1)°
V = 1433.60 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 100 K
0.58 × 0.13 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.795, T _max = 0.980
24411 measured reflections
8309 independent reflections
6194 reflections with I > 2˘I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.104
S = 1.04
8309 reflections
375 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.50 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/S1600536809014512/lh2805sup1.cif

e-65-o1119-sup1.cif^{(31.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014512/lh2805Isup2.hkl

e-65-o1119-Isup2.hkl^{(406.4KB, 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
N2A—H2NA⋯O1Bⁱ	0.81	2.20	3.003 (4)	171
C10A—H10A⋯O2Aⁱⁱ	0.95	2.42	3.235 (3)	144
C12B—H12B⋯O1Aⁱⁱ	0.95	2.48	3.233 (6)	137
C9B—H9BA⋯O1Bⁱⁱⁱ	0.95	2.55	3.369 (9)	145

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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. 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 (I).

The title compound, (Fig. I), is a novel sulfonamide derivative. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable with the related structures (Kia et al. 2008a,b; Mehrabi et al., 2008; Ali et al. 2007). The asymmetric unit of the title compound comprises two crystallographically independent molecules and a water molecule of crystallization which is partially occupied. One of the molecules of the title compound is disordered over two positions with a refined site-occupancy ratio of 0.605 (10)/0.395 (10). Intermolecular N—H···O and C—H···O hydrogen bonds link the neighbouring molecules together (Table 1). The dihedral angles between the two benzene rings in molecules A, B and C are 67.8 (3), 74.6 (5) and 84.96 (11)°, respectively. The crystal structure is further stabilized by intermolecular π-π interactions [Cg1···Cg 2^iv = 3.749 (3) Å, (iv) -1 + x, -1 + y, z; Cg2···Cg3^v = 3.805 (5) Å, (v) 1 + x, 1 + y, z; Cg1, Cg2 and Cg3 are the centroids of the C1B–C6B, C1A–C6A, and C1C–C6C benzene rings].

Experimental

p-Tosylhydrazine (2 mmol) was added to a 50 ml refluxing ethanolic solution of 4-chlorobenzaldehyde (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.