1-(3-Cyano­phen­yl)-3-(2-furo­yl)thio­urea

Jahyr E Theodoro; Yvonne Mascarenhas; Javier Ellena; Osvaldo Estévez-Hernández; Julio Duque

doi:10.1107/S1600536808016012

. 2008 Jun 7;64(Pt 7):o1193. doi: 10.1107/S1600536808016012

1-(3-Cyanophenyl)-3-(2-furoyl)thiourea

Jahyr E Theodoro ^a, Yvonne Mascarenhas ^b, Javier Ellena ^a, Osvaldo Estévez-Hernández ^c, Julio Duque ^c,^*

PMCID: PMC2961779 PMID: 21202835

Abstract

The title compound, C₁₃H₉N₃O₂S, was synthesized from furoyl isothiocyanate and 3-aminobenzonitrile in dry acetone. The thiourea group is in the thioamide form. The thiourea fragment makes dihedral angles of 3.91 (16) and 37.83 (12)° with the ketofuran group and the benzene ring, respectively. The molecular geometry is stabilized by N—H⋯O hydrogen bonds. In the crystal structure, centrosymmetrically related molecules are linked by two intermolecular N—H⋯S hydrogen bonds to form dimers.

Related literature

For general background, see: Aly et al. (2007 ▶); Koch (2001 ▶). For related structures, see: Dago et al. (1987 ▶); Otazo-Sánchez et al. (2001 ▶); Pérez et al. (2008 ▶); Duque et al. (2008 ▶). For the synthesis, see: Otazo-Sánchez et al. (2001 ▶).

Experimental

Crystal data

C₁₃H₉N₃O₂S
M _r = 271.29
Monoclinic,
a = 16.7375 (5) Å
b = 3.8789 (1) Å
c = 19.6739 (5) Å
β = 96.956 (1)°
V = 1267.89 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 294 K
0.16 × 0.04 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
4807 measured reflections
2684 independent reflections
1908 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.208
S = 1.08
2684 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: COLLECT (Enraf–Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016012/rz2219sup1.cif

e-64-o1193-sup1.cif^{(15.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016012/rz2219Isup2.hkl

e-64-o1193-Isup2.hkl^{(129KB, 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
N1—H1⋯O2	0.86	2.28	2.701 (5)	110
N1—H1⋯S1ⁱ	0.86	2.80	3.629 (4)	163
N2—H2⋯O1	0.86	1.90	2.622 (4)	141

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Crystallography Group, São Carlos Physics Institute, USP, and acknowledge financial support from the Brazilian agency CNPq.

supplementary crystallographic information

Comment

The importance of aroylthioureas is found largely in heterocyclic syntheses and many of these substrates have interesting biological activities. Aroylthioureas have also been found to have applications in metal complexes and molecular electronics (Aly et al., 2007). Structural determinations of this kind of derivatives shed more light on the chemistry of aroylthiourea compounds and their wide variety of applications. The title compound (Fig. 1) is another example of our newly synthesized furoylthiourea derivatives.

The title compound crystallizes in the thioamide form. The bond lengths are within the ranges observed for similar compounds (Koch, 2001). The C2—S1 and C1—O1 bonds (Table 1) both show the expected double-bond character. The short values of the C2—N1 (1.347 (5) Å), C2—N2 (1.348 (5) Å) and C1—N1 (1.368 (5) Å) bonds indicate partial double bond character. These results can be explained by the existence of resonance in this part of the molecule. The furan carbonyl group is nearly coplanar with the plane of the thiourea fragment (dihedral angle 3.39(16°), whereas the benzene ring is inclined by 37.83 (12)°. The geometry in the thiourea group is stabilized by the N2—H2···O1 and N1—H1···O2 intramolecular hydrogen bonds (Fig. 1 and Table 2). The crystal structure is stabilized by two intermolecular N1—H1···S1 hydrogen bonds (Fig. 2 and Table 2) between centrosymmetrically related molecules forming dimers stacked along the [010] direction.

Experimental

The title compound was synthesized according to a previous report (Otazo-Sánchez et al., 2001), by converting furoyl chloride into furoyl isothiocyanate and then condensing with 3-aminobenzonitrile. The resulting solid product was crystallized from ethanol yielding X-ray quality single crystals (m.p 148–149 °C). Elemental analysis (%) for C₁₃H₉N₃O₂S calculated: C 57.56, H 3.32, N 15.50, S 11.81; found: C 57.77, H 3.34, N 15.79, S 11.73.