1-Benzoyl-3-(5-quinol­yl)thio­urea

Wen-Hu Du; Chang-Mei Wei; Wei-Feng Wang

doi:10.1107/S1600536809000932

. 2009 Jan 14;65(Pt 2):o308. doi: 10.1107/S1600536809000932

1-Benzoyl-3-(5-quinolyl)thiourea

Wen-Hu Du ^a,^b, Chang-Mei Wei ^b,^c,^*, Wei-Feng Wang ^a,^b

PMCID: PMC2968342 PMID: 21581917

Abstract

The title compound, C₁₇H₁₃N₃OS, was obtained by the reaction of benzoyl chloride, ammonium thiocyanate and 5-aminoquinoline in the presence of polyethyleneglycol-400 (PEG-400) as a phase-transfer catalyst. The compound crystallized as discrete molecules linked by N—H⋯N and C—H⋯N hydrogen bonds involving all the potential donors, generating sheets parallel to (100). An intramolecular N—H⋯O bond is also present.

Related literature

For the biological activity of acyl thioureas, see: Hackmann (1960 ▶); Sarkis & Faisal (1985 ▶). For their application in the synthesis of supramolecular complexes, see: Pluta & Sadlej (2001 ▶); Kaminsky et al. (2002 ▶). For a related structure, see: Xue et al. (2004 ▶).

Experimental

Crystal data

C₁₇H₁₃N₃OS
M _r = 307.36
Monoclinic,
a = 5.0875 (1) Å
b = 16.1718 (4) Å
c = 18.2847 (4) Å
β = 95.892 (2)°
V = 1496.41 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.939, T _max = 0.969
13322 measured reflections
3411 independent reflections
2184 reflections with I > 2σ(I)
R _int = 0.032
3 standard reflections every 97 reflections intensity decay: 2.1%

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.129
S = 1.04
3411 reflections
207 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000932/hg2453sup1.cif

e-65-0o308-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000932/hg2453Isup2.hkl

e-65-0o308-Isup2.hkl^{(167.3KB, 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—H6⋯N3ⁱ	0.825 (17)	2.283 (17)	3.100 (3)	170.5 (18)
N2—H7⋯O1	0.91 (3)	1.84 (3)	2.619 (3)	143 (3)
C6—H5⋯N3ⁱ	0.93	2.46	3.252 (3)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to the Science Foundation of Jiangsu Education Bureau (05KJD 150039), the Professor Foundation of Huaiyin Teachers College (05 HSJS018) and the Science Foundation of Jangsu Key Laboratory for the Chemistry of Low-Dimensional Materials (JSKC 06028) for financial support.

supplementary crystallographic information

Comment

Acyl thioureas have extensive biological activities such as bacteriostasis, weeding (Hackmann, 1960) and plant growth regulating (Sarkis & Faisal, 1985). In addition, acyl thioureas are excellent ligands, and have been widely applied in synthesis of supramolecular complexes (Pluta & Sadlej, 2001; Kaminsky et al., 2002). The title compound, (I) crystallizes as discrete molecules (Fig. 1). The full molecule is a big conjugated system because the bond lengths of C1—C7, C7—N1, C8—N1, C8—N2 and C9—N2 become shorter than standard values, and the bond lengths of C7—O1 and C8—S1 become longer than standard values. In (I) the torsion angle for C17—C9—N2—C8 of -78.2 (3)° indicates the quinoline ring is approximately orthogonal to the rest of the molecule. The molecules in (I) are linked by N1—H6···N3, N2—H7···O1 and C6—H5···N3 hydrogen bonds involving all the potential donors, generating sheets parallel to (100), as shown in Fig. 2. In addition, the bond lengths of S—C (1.655 (2)Å) and O—C(1.223 (2)Å) in (I) are longer than the bond lengths of S—C(1.6503Å) and O—C(1.201Å) in N-(4,6-dimethylpyrimidin-2-ylcarbamothioyl)benzamide (Xue et al., 2004)

Experimental

The title compound was synthesized as following. A mixture of benzoyl chloride (1400 mg, 10 mmol), ammonium thiocyanate (1140 mg, 15 mmol), 5-aminoquinoline (1300 mg, 9 mmol) and dichloromethane (50 ml) in the presence of PEG-400 (1200 mg, 3 mmol) as phase transfer catalyst at room temperature for 8h with stirring. The reaction mixture was evaporated to give a residue. Singles crystals suitable for X-ray analysis were obtained by slow evaporation of a mixture solution of dichloromethane and ethanol.