2-Hydr­oxy-5-nitro­benzaldehyde thio­semicarbazone

Abeer A Alhadi; Hapipah M Ali; Subramaniam Puvaneswary; Ward T Robinson; Seik Weng Ng

doi:10.1107/S1600536808022976

. 2008 Jul 26;64(Pt 8):o1606. doi: 10.1107/S1600536808022976

2-Hydroxy-5-nitrobenzaldehyde thiosemicarbazone

Abeer A Alhadi ^a, Hapipah M Ali ^a, Subramaniam Puvaneswary ^a, Ward T Robinson ^a, Seik Weng Ng ^a,^*

PMCID: PMC2962218 PMID: 21203299

Abstract

The molecule of the title compound, C₈H₈N₄O₃S, is planar. Adjacent molecules are linked through O—H⋯S, N—H⋯S and N—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the structure of 2-hydroxybenzaldehyde thiosemicarbazone, see: Chattopadhyay et al. (1988 ▶).

Experimental

Crystal data

C₈H₈N₄O₃S
M _r = 240.24
Monoclinic,
a = 12.6157 (3) Å
b = 5.4815 (2) Å
c = 14.2397 (2) Å
β = 94.039 (2)°
V = 982.27 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 100 (2) K
0.49 × 0.01 × 0.01 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.856, T _max = 0.997
9462 measured reflections
2247 independent reflections
1725 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.04
2247 reflections
161 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.23 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 global, I. DOI: 10.1107/S1600536808022976/rk2102sup1.cif

e-64-o1606-sup1.cif^{(14.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022976/rk2102Isup2.hkl

e-64-o1606-Isup2.hkl^{(110.5KB, 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—H1⋯S1ⁱ	0.84 (1)	2.34 (1)	3.175 (2)	170 (3)
N3—H31⋯S1ⁱⁱ	0.85 (1)	2.50 (1)	3.337 (2)	167 (2)
N4—H41⋯O2ⁱⁱⁱ	0.85 (1)	2.14 (1)	2.987 (2)	172 (3)
N4—H42⋯O3^iv	0.85 (1)	2.31 (2)	3.044 (2)	144 (2)

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

Acknowledgments

The authors thank the Science Fund (grant Nos. 12-02-03-2031 and 12-02-03-2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

Salicylaldehyde thiosemicarbazone uses its 2-hydroxy group to form an intramolecular hydrogen bond (Chattopadhyay et al., 1988). In the present compound, the electron-withdrawing nitro group that is para to the hydroxy group renders the hydroxy group much more acidic, so that the compound (Scheme) is able to use the hydroxy group to form a hydrogen bond to an adjacent molecule instead (Fig. 1).

Experimental

The Schiff base was prepared by refluxing thiosemicarbazide (0.30 g, 3.3 mmol) and 5-nitro-2-hydroxybenzaldehyde (0.55 g, 3.3 mmol) in ethanol for 2 h. The product was recrystallized from ethanol.