(E)-1-(3-Eth­oxy-2-hy­droxy­benzyl­idene)thio­semicarbazide

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

doi:10.1107/S1600536812000487

. 2012 Jan 11;68(Pt 2):o340–o341. doi: 10.1107/S1600536812000487

(E)-1-(3-Ethoxy-2-hydroxybenzylidene)thiosemicarbazide

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

PMCID: PMC3275025 PMID: 22346970

Abstract

The title compound, C₁₀H₁₃N₃O₂S, crystallizes with two independent molecules (A and B) in the asymmetric unit. In the crystal, the A and B molecules are linked via pairs of N—H⋯O and O—H⋯S hydrogen bonds, forming dimers with R ₂ ²(14) and R ₂ ²(6) ring motifs. These dimers are linked via a pair of N—H⋯S hydrogen bonds with an R ₂ ²(8) ring motif, forming chains propagating along the c-axis direction. The crystal was refined as an inversion twin with a final BASF ratio of 0.54 (11):0.46 (11).

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). 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: for example, Maccioni et al. (2003 ▶); Ferrari et al. (2000 ▶). For related structures, see: Kargar et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₀H₁₃N₃O₂S
M _r = 239.29
Monoclinic,
a = 6.0728 (3) Å
b = 16.1595 (8) Å
c = 12.8490 (6) Å
β = 90.238 (3)°
V = 1260.91 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 291 K
0.24 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.800, T _max = 0.926
12062 measured reflections
5428 independent reflections
2303 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.119
S = 0.92
5428 reflections
293 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 2232 Friedel pairs
Flack parameter: 0.54 (11)

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/S1600536812000487/su2360sup1.cif

e-68-0o340-sup1.cif^{(29.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000487/su2360Isup2.hkl

e-68-0o340-Isup2.hkl^{(265.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812000487/su2360Isup3.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—H1O⋯S2ⁱ	0.83	2.53	3.180 (4)	135
O3—H3O⋯S1ⁱⁱ	0.83	2.43	3.143 (4)	145
N2—H2N⋯O3ⁱ	0.90	2.20	2.954 (6)	142
N5—H5N⋯O1ⁱⁱ	0.87	2.17	3.009 (5)	160
N3—H3NB⋯S2ⁱⁱⁱ	0.90	2.53	3.403 (4)	166
N6—H6NB⋯S1^iv	0.88	2.55	3.398 (5)	161

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

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). Herein, we report on the crystal structure of the new title thiosemicarbazone compound.

The title compound crystallized with two independent molecules (A and B) in the asymmetric unit, Fig. 1. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those observed for related structures (Kargar et al., 2010a,b).

In the crystal, the A and B molecules are linked via pairs of N-H···O and O-H···S hydrogen bonds (Table 1 and Fig. 2) to form dimers, with R²₂(14) and R²₂(6) ring motifs (Bernstein et al., 1995). These dimers are further linked via a pair of N-H···S hydrogen bonds, with an R²₂(8) ring motif, to form chains that extend in direction [0 0 1] (Table 1 and Fig. 2).

The crystal was refined as an inversion twin with a final refined BASF ratio of 0.54 (11)/0.46 (11) for 2232 Friedel pairs.

Experimental

A mixture of 3-ethoxysalicylalehyde (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.