2,5-Dihydroxy­benzaldehyde 4-methyl­thio­semicarbazone

Kong Wai Tan; Chew Hee Ng; Mohd Jamil Maah; Seik Weng Ng

doi:10.1107/S1600536808018801

. 2008 Jun 28;64(Pt 7):o1344. doi: 10.1107/S1600536808018801

2,5-Dihydroxybenzaldehyde 4-methylthiosemicarbazone

Kong Wai Tan ^a, Chew Hee Ng ^b, Mohd Jamil Maah ^c,^*, Seik Weng Ng ^c

PMCID: PMC2961871 PMID: 21202966

Abstract

The planar molecules of the title compound, C₉H₁₁N₃O₂S, are linked into a supramolecualr chain via O—H⋯S hydrogen bonds. These chains are connected into a two-dimensional array via N—H⋯O hydrogen bonds; an intramolecular O—H⋯N hydrogen bond is also present.

Related literature

For the medicinal activity of 2,5-dihydroxybenzaldehyde thiosemicarbazone, see: Libermann et al. (1953 ▶); Taniyama & Tanaka (1965 ▶); Xue et al. (2007 ▶). For the structure of 2-hydroxybenzaldehyde 4-methylthiosemicarbazone, see: Vrdoljak et al. (2005 ▶). For the structure of 3,4-dihydroxybenzaldehyde 4-ethylthiosemicarbazone, see: Kayed et al. (2008 ▶).

Experimental

Crystal data

C₉H₁₁N₃O₂S
M _r = 225.27
Triclinic,
a = 5.9932 (4) Å
b = 8.5207 (6) Å
c = 10.3272 (6) Å
α = 78.552 (4)°
β = 74.181 (4)°
γ = 81.743 (4)°
V = 495.06 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 (2) K
0.24 × 0.16 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.929, T _max = 0.994
4189 measured reflections
2258 independent reflections
1580 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.123
S = 1.03
2258 reflections
153 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018801/tk2278sup1.cif

e-64-o1344-sup1.cif^{(14.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018801/tk2278Isup2.hkl

e-64-o1344-Isup2.hkl^{(111KB, 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—H1o⋯N3	0.84 (3)	1.97 (2)	2.698 (3)	144 (3)
O2—H2o⋯S1ⁱ	0.84 (3)	2.46 (2)	3.182 (2)	144 (3)
N2—H2n⋯O1ⁱⁱ	0.84 (3)	2.47 (3)	3.111 (3)	134 (3)

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

Acknowledgments

We thank the University of Malaya (P0265/2007 A) for supporting this study. KWT thanks the Ministry of Higher Education for a SLAI scholarship.

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) possesses useful medicinal properties (Libermann et al., 1953; Taniyama & Tanaka, 1965; Xue et al., 2007). The molecules are linked into supramolecular chains by O-H···S hydrogen bonds involving the O2-hydroxy group, Table 1. The hydrogen-bonded chains are consolidated into a layer motif via N-NH···O hydrogen bond, involving the O1-hydroxy group. An intramolecular N-H···O hydrogen bond, also involving the O1-hydroxy group is also noted. In contrast, 2-hydroxybenzaldehyde 4-methylthiosemicarbazone, which features an intramolecular O–H···N hydrogen bond, adopts a chain structure (Vrdoljak et al., 2005) as it lacks a second hydroxy substituent for layer formation.

Experimental

4-Methylthiosemicarbazide (0.11 g, 1 mmol) and 2,5-dihydroxybenzaldehyde (0.14 g, 1 mmol) were heated in ethanol (10 ml) for 1 h. Slow evaporation of the solvent yielded yellow crystals of (I).