4-(Dimethyl­amino)benzaldehyde 4-ethyl­thio­semicarbazone

Abdussalam Salhin; Norfarhah Abdul Razak; I A Rahman

doi:10.1107/S1600536808037148

. 2008 Nov 13;64(Pt 12):o2353. doi: 10.1107/S1600536808037148

4-(Dimethylamino)benzaldehyde 4-ethylthiosemicarbazone

Abdussalam Salhin ^a,^*, Norfarhah Abdul Razak ^a, I A Rahman ^a

PMCID: PMC2960080 PMID: 21581327

Abstract

The title thiosemicarbazone derivative, C₁₂H₁₈N₄S, features intramolecular N—H⋯N and C—H⋯S hydrogen bonds which generate S(5) ring motifs. The dihedral angle between the benzene ring and the thiourea unit is 6.30 (6)° indicating planarity in the molecule. Intermolecular N—H⋯S hydrogen bonds generate dimers with an R ₂ ²(8) ring motif. The methyl group of the N-ethyl residue is disordered and was refined with site occupancies of 0.521 (5) and 0.479 (5).

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures and applications see: Beraldo et al. (2001 ▶); Kayed et al. (2008 ▶); Valdes-Martinez et al. (1990 ▶).

Experimental

Crystal data

C₁₂H₁₈N₄S
M _r = 250.36
Monoclinic,
a = 9.3687 (2) Å
b = 14.1872 (3) Å
c = 10.2318 (2) Å
β = 96.699 (1)°
V = 1350.68 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 (1) K
0.59 × 0.36 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.879, T _max = 0.953
30229 measured reflections
6825 independent reflections
5566 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.119
S = 1.04
6825 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037148/tk2323sup1.cif

e-64-o2353-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037148/tk2323Isup2.hkl

e-64-o2353-Isup2.hkl^{(334KB, 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
N3—H1N3⋯S1ⁱ	0.891 (15)	2.613 (15)	3.4910 (7)	168.8 (12)
N4—H1N4⋯N2	0.885 (14)	2.193 (14)	2.6140 (10)	108.7 (11)
C9—H9B⋯S1	0.96	2.78	3.1225 (9)	102

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Malysian Government and Universiti Sains Malaysia for Science Fund grant No. 1001/229/PKIMIA/811055

supplementary crystallographic information

Comment

Thiosemicarbazones have been a subject of extensive investigation (Kayed et al., 2008) because of their ability to coordinate metal ions and their wide range of chemical and biological activities (Valdes-Martinez et al., 1990 & Beraldo et al., 2001). We present herein the X-ray structure of the title thiosemicarbazone derivative, (I).

Compound (I), Fig. I, displays bond lengths and angles comparable to those in related structures (Beraldo et al., 2001; Kayed et al., 2008; Valdes-Martinez et al., 1990). Intramolecular N—H···N and C—H···S contacts generate S(5) ring motifs (Bernstein et al. 1995), Table 1. The dihedral angle between the phenyl ring and the thiourea unit is 6.30 (6)° which indicates the molecule is almost planar. Intermolecular N—H···S hydrogen bonds generate R₂²(8) ring motifs to link molecules into dimers, Fig. 2. The methyl group of the N-ethyl residue is disordered and was refined with site occupancies of 0.521 (5)/0.479 (5).

Experimental

To 4-ethyl-3-thiosemicarbazide (ca. 0.119 g, 1 mmol) dissolved in ethanol (10 ml) was added dropwise an ethanol solution (5 ml) of 4-dimethylaminobenzaldehyde (0.149 g, 1 mmol) with continuous stirring. The solution was heated on a water bath for few minutes until the solution became clear. After cooling to room temperature, yellow crystals of (I) appeared.