1-(2,6-Dichloro­benzo­yl)-3-(3,5-dichloro­phen­yl)thio­urea

M Khawar Rauf; Michael Bolte; Amin Badshah

doi:10.1107/S1600536808042736

. 2008 Dec 20;65(Pt 1):o177. doi: 10.1107/S1600536808042736

1-(2,6-Dichlorobenzoyl)-3-(3,5-dichlorophenyl)thiourea

M Khawar Rauf ^a, Michael Bolte ^b, Amin Badshah ^a,^*

PMCID: PMC2968087 PMID: 21581633

Abstract

The crystal structure of the title compound, C₁₄H₈Cl₄N₂OS, is composed of discrete molecules with bond lengths and angles quite typical for thiourea compounds of this class. The plane containing the central SONNCC atom set subtends a dihedral angle of 31.47 (3)° with the benzene ring. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation and the molecules form centrosymmetric dimers via intermolecular N—H⋯S hydrogen bonds.

Related literature

For general background, see: Upadlgaya & Srivastava (1982 ▶); Wegner et al. (1986 ▶); Krishnamurthy et al. (1999 ▶). For related structures, see: Khawar Rauf et al. (2006a ▶, 2007 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For bond lengths and angles in N,N′-disubstituted thiourea compounds, see: Arslan et al. (2004 ▶); Khawar Rauf et al. (2006b ▶); Yamin & Yusof, (2003 ▶).

Experimental

Crystal data

C₁₄H₈Cl₄N₂OS
M _r = 394.08
Monoclinic,
a = 14.7737 (13) Å
b = 10.3744 (6) Å
c = 10.6935 (11) Å
β = 97.250 (7)°
V = 1625.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 173 (2) K
0.42 × 0.38 × 0.21 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T _min = 0.715, T _max = 0.841
12823 measured reflections
3724 independent reflections
3306 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.087
S = 1.05
3724 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042736/fl2225sup1.cif

e-65-0o177-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042736/fl2225Isup2.hkl

e-65-0o177-Isup2.hkl^{(182.6KB, 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
N2—H2⋯O1	0.91 (2)	1.89 (2)	2.6581 (17)	141 (2)
N1—H1⋯S1ⁱ	0.82 (2)	2.57 (2)	3.3653 (14)	163 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

MKR is grateful to the HEC-Pakistan for financial support for the PhD program under scholarship No. [ILC–0363104].

supplementary crystallographic information

Comment

Aliphatic and acylthioureas are well known for their fungicidal,antiviral, pesticidal and plant-growth regulating activities (Upadlgaya & Srivastava, 1982; Wegner et al., 1986). Symmetrical and unsymmetrical thioureas have shown antifungal activity against the plant pathogens Pyricularia oryzae and Drechslera oryzae (Krishnamurthy et al., 1999). The background to this study has been set out in our previous work on the structural and biological chemistry of chloro substituted N,N'-disubstituted thioureas (Khawar Rauf et al., 2006a; 2007).The biological studies of these thiourea derivatives are under investigation. Herein, as a continuation of these studies, the structure of the title compound (I) is described (Fig. 1). Bond lengths and angles, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006b; Arslan et al., 2004; Yamin & Yusof, 2003).The molecule exists in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. The thiocarbonyl and carbonyl groups are almost coplanar. The molecule features an intramolecular N—H···O hydrogen bond and in the crystal structure, molecules associate via N—H···S intermolecular hydrogen bonds to form centrosymmetric dimers (Table 1; Fig 2).In addition to the intramolecular hydrogen bond, O1 is involved in a short O···Cl contact [O1···Cl2ⁱ: 3.0936 (14) Å, symmetry operator i: 1 - x, 1 - y, 1 - z].

Experimental

Freshly prepared 2,6-dichlorobenzoyl isothiocyanate (2.32 g, 10 mmol) was stirred in acetone (40 ml) for 20 minutes. Neat 3,5-dichloroaniline (1.62 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was then poured into acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ 1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall yield of 80%.