(E)-1-(2-Hy­droxy-5-meth­oxy­benzyl­idene)thio­semicarbazide

Amir Adabi Ardakani; Hadi Kargar; Reza Kia; Muhammad Nawaz Tahir

doi:10.1107/S1600536811056182

. 2012 Jan 11;68(Pt 2):o324–o325. doi: 10.1107/S1600536811056182

(E)-1-(2-Hydroxy-5-methoxybenzylidene)thiosemicarbazide

Amir Adabi Ardakani ^a,^*, Hadi Kargar ^b, Reza Kia ^c,^d, Muhammad Nawaz Tahir ^e,^*

PMCID: PMC3275013 PMID: 22346958

Abstract

In the title molecule, C₉H₁₁N₃O₂S, an intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked via pairs of N—H⋯S interactions, forming inversion dimers with R ₂ ²(8) ring motifs. These dimers are further linked via N—H⋯S and N—H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (100). The crystal structure is further stabilized by intermolecular π–π interactions [centroid–centroid distance = 3.7972 (9) Å].

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to thiosemicarbazones in coordination chemistry, see: Casas et al. (2000 ▶). For their biological applications, see: Maccioni et al. (2003 ▶); Ferrari et al. (2000 ▶). For related structures, see: Kargar et al. (2010a ▶,b ▶); Adabi Ardakani et al. (2012 ▶).

Experimental

Crystal data

C₉H₁₁N₃O₂S
M _r = 225.27
Monoclinic,
a = 7.4878 (2) Å
b = 9.9880 (2) Å
c = 14.3754 (3) Å
β = 91.846 (1)°
V = 1074.55 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 291 K
0.24 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.800, T _max = 0.926
10176 measured reflections
2673 independent reflections
2365 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.110
S = 1.07
2673 reflections
138 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811056182/su2361sup1.cif

e-68-0o324-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056182/su2361Isup2.hkl

e-68-0o324-Isup2.hkl^{(131.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811056182/su2361Isup3.cml

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—H1⋯N1	0.82	1.97	2.6844 (15)	146
N2—H2⋯S1ⁱ	0.86	2.61	3.3706 (12)	148
N3—H3A⋯S1ⁱⁱ	0.86	2.66	3.2706 (12)	129
N3—H3B⋯O1ⁱⁱⁱ	0.86	2.11	2.9604 (17)	172

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

Acknowledgments

AAA thanks the Islamic Azad University, Ardakan Branch (this paper was extracted from the research project). HK thanks PNU for financial support. MNT thanks Sargodha University for research facilities.

supplementary crystallographic information

Comment

Thiosemicarbazones constitute an important class of N,S donor ligands due to their propensity to react with a wide range of metals (Casas et al., 2000). Thiosemicarbazones exhibit various biological activities and have therefore attracted considerable pharmaceutical interest (Maccioni et al., 2003; Ferrari et al., 2000). We report herein on the synthesis and crystal structure of the title a hydrazone Schiff base compound.

The asymmetric unit of the title compound, Fig. 1, comprises a hydrazone Schiff base ligand. The bond lengths and angles are within the normal ranges and are comparable to those reported for related structures (Kargar et al., 2010a,b; Adabi et al., 2012). An intramolecular O—H···N hydrogen bond (Table 1) generates an S(6) ring motif (Bernstein et al., 1995).

In the crystal, pairs of intermolecular N—H···S hydrogen bonds make inversion dimers with an R²₂(8) ring motif. Intermolecular N—H···S and N—H···O hydrogen bonds link neighbouring molecules into a two-dimensional extended network parallel to (1 0 0). For details of the hydrogen bonding see Table 1, and Fig. 2. The crystal structure is further stabilized by an intermolecular π···π interaction [Cg1···Cg1ⁱ = 3.7972 (9)Å; (i) -x+1, -y+1, -z+2; Cg1 is the centroid of ring (C1–C6)].

Experimental

A mixture of 5-methoxysalicylalehyde (0.01 mol) and hydrazinecarbothioamide (0.01 mol) in 20 ml of ethanol was refluxed for about 2 h. On cooling, the solid separated was filtered and recrystallized from ethanol. Colourless plate-like crystals of the title compound, suitable for X-ray diffraction, were obtained by slow evaporation of a solution in ethanol.