1-(3-Chloro­benzo­yl)-3-(2,3-dimethyl­phen­yl)thio­urea

M Khawar Rauf; Michael Bolte; Amin Badshah

doi:10.1107/S1600536809000063

. 2009 Jan 8;65(Pt 2):o240. doi: 10.1107/S1600536809000063

1-(3-Chlorobenzoyl)-3-(2,3-dimethylphenyl)thiourea

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

PMCID: PMC2968148 PMID: 21581857

Abstract

The title molecule, C₁₆H₁₅ClN₂OS, exists in the solid state in its thione form with typical thiourea C—S and C—O bonds lengths, as well as shortened C—N bonds. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation and intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers. The dihedral angle between the aromatic rings is 50.18 (5)°.

Related literature

For related compounds, see: Khawar Rauf et al. (2006a ▶,b ▶,c ▶,d ▶). For reference bond-length data, see: Allen (2002 ▶).

Experimental

Crystal data

C₁₆H₁₅ClN₂OS
M _r = 318.81
Triclinic,
a = 8.1315 (9) Å
b = 9.3906 (12) Å
c = 10.5310 (12) Å
α = 93.296 (8)°
β = 92.623 (8)°
γ = 102.579 (9)°
V = 782.14 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 173 (2) K
0.46 × 0.42 × 0.41 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T _min = 0.846, T _max = 0.861
8257 measured reflections
3066 independent reflections
2846 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.085
S = 1.04
3066 reflections
201 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.33 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/S1600536809000063/bv2114sup1.cif

e-65-0o240-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000063/bv2114Isup2.hkl

e-65-0o240-Isup2.hkl^{(150.4KB, 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	0.86 (2)	1.99 (2)	2.6840 (16)	137.7 (17)
N1—H1⋯S1ⁱ	0.836 (19)	2.636 (19)	3.4376 (13)	161.2 (15)

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Symmetry code: (i) Inline graphic .

Acknowledgments

MKR is grateful to the HEC, Pakistan, for financial support for a PhD programme under scholarship No. ILC-0363104.

supplementary crystallographic information

Comment

The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Khawar Rauf et al., 2006a,b,c,d). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the table of selected geometric parameters, 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., 2006a).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 dihedral angle between the aromatic rings is 50.18 (5)°. An intramolecular N—H···O hydrogen bond is present (Table 2), forming a six-membered ring commonly observed in this class of compounds (Khawar Rauf et al., 2006d). Intermolecular N—H···S hydrogen bonds link the molecules to form centrosymmetric dimers.

Experimental

Freshly prepared 3-chlorobenzoyl isothiocyanate (2.0 g, 10 mmol) was stirred in acetone (40 ml) for 20 min. Neat 2,3-dimethylaniline (1.62 g, 10 mmol) was then added and the resulting mixture was stirred for 1.5 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 90%. Full spectroscopic and physical characterization will be reported elsewhere.