1-(4-Chloro­phen­yl)-3-(2-thienylcarbon­yl)thio­urea

Sohail Saeed; Naghmana Rashid; Wing-Tak Wong

doi:10.1107/S1600536810013863

. 2010 Apr 24;66(Pt 5):o1162. doi: 10.1107/S1600536810013863

1-(4-Chlorophenyl)-3-(2-thienylcarbonyl)thiourea

Sohail Saeed ^a,^*, Naghmana Rashid ^a, Wing-Tak Wong ^b

PMCID: PMC2979166 PMID: 21579205

Abstract

The title compound, C₁₂H₉ClN₂OS₂, exists in the thioamide form with an intramolecular N—H⋯O hydrogen bond across the thiourea and the carbonyl group. The dihedral angle between the rings is 10.36 (11)°. In the crystal structure, molecules are linked into chains by weak intermolecular C—H⋯Cl hydrogen-bonding interactions.

Related literature

For general background to the biological activity of thiourea derivatives, see: Xu et al. (2004 ▶); Gu et al. (2007 ▶). For related structures, see: Saeed et al. (2008 ▶, 2009 ▶). For the cytotoxicity of anticancer drugs to normal cells in cancer therapy, see: Saeed et al. (2010 ▶).

Experimental

Crystal data

C₁₂H₉ClN₂OS₂
M _r = 296.78
Monoclinic,
a = 4.6552 (7) Å
b = 11.660 (2) Å
c = 23.630 (4) Å
β = 95.626 (2)°
V = 1276.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 300 K
0.42 × 0.19 × 0.08 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.783, T _max = 0.953
8549 measured reflections
3102 independent reflections
2578 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.107
S = 1.07
3102 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT and CrystalStructure (Rigaku/MSC and Rigaku, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013863/lx2142sup1.cif

e-66-o1162-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013863/lx2142Isup2.hkl

e-66-o1162-Isup2.hkl^{(152.3KB, 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—H1N⋯O1	0.87 (2)	1.91 (2)	2.651 (2)	143 (2)
C12—H12⋯Cl1ⁱ	0.93	2.69	3.523 (2)	149

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Department of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad, and The Hong Kong Polytechnic University for providing laboratory and analytical facilities.

supplementary crystallographic information

Comment

Thiourea and its derivatives are an important class of organic compounds in which sulfur is the major ligand atom which plays an important role in coordination chemistry with transition metals. Thiourea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. Thioureas are also known to exhibit a wide range of biological activities including anticancer (Saeed et al., 2010), antifungal (Saeed et al., 2008), antiviral, antibacterial, anti-tubercular, anti-thyroidal, herbicidal and insecticidal activities, organocatalyst (Gu et al., 2007) and as agrochemicals (Xu et al., 2004).

The 4-chlorophenyl ring is slightly twisted {15.04 (8)°} from the thiourea plane. The thioureido group is also slightly twisted {5.0 (1)°} from the thiophene ring plane of S2/C9/C10/C11/C12. The molecular packing (Fig. 2) exhibits the thioamide form with an intramolecular N–H···O hydrogen bond across the thiourea system, with a N1–H1N···O1 (Table 1). The crystal packing (Fig. 2) is stabilized by weak intermolecular C–H···Cl hydrogen bonds between the thiophene H atom and the chlorine of an adjacent molecule, with a C12–H12···Cl1ⁱ (Table 1).

Experimental

A solution of 2-thiophenecarbonyl chloride (0.01 mol) in anhydrous acetone (80 ml) was added dropwise to a suspension of ammonium thiocyanate (0.01 mol) in anhydrous acetone (50 ml) and the reaction mixture was refluxed for 50 minutes. After cooling to room temperature, a solution of 4-chloroaniline (0.01 mol) in dry acetone (25 ml) was added and the resulting mixture refluxed for 2 h. The reaction mixture was poured into five times its volume of cold water, upon which the thiourea precipitated. The product was recrystallized from ethanol as white block crystals.