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

M Khawar Rauf; Masahiro Ebihara; Amin Badshah

doi:10.1107/S1600536812048209

. 2012 Nov 30;68(Pt 12):o3483. doi: 10.1107/S1600536812048209

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

M Khawar Rauf ^a,^*, Masahiro Ebihara ^b, Amin Badshah ^a,^*

PMCID: PMC3589055 PMID: 23476291

Abstract

The dihedral angle between the two phenyl groups in the title compound, C₁₆H₁₅ClN₂OS, is 14.88 (4)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, pairs of N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For background and a related structure, see: Rauf et al. (2012 ▶). For a description of the Cambridge Structural Database, see: Allen et al. (2002 ▶).

Experimental

Crystal data

C₁₆H₁₅ClN₂OS
M _r = 318.81
Triclinic,
a = 7.489 (3) Å
b = 9.338 (4) Å
c = 13.274 (5) Å
α = 65.674 (13)°
β = 69.975 (16)°
γ = 73.639 (17)°
V = 783.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 123 K
0.50 × 0.35 × 0.28 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
6180 measured reflections
3506 independent reflections
3373 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.090
S = 1.08
3506 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: Yadokari-XG (Wakita, 2001 ▶; Kabuto et al., 2009 ▶).

Supplementary Material

Click here for additional data file.^{(18KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048209/hg5274sup1.cif

e-68-o3483-sup1.cif^{(18KB, cif)}

Click here for additional data file.^{(171.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048209/hg5274Isup2.hkl

e-68-o3483-Isup2.hkl^{(171.9KB, hkl)}

Click here for additional data file.^{(5.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812048209/hg5274Isup3.cml

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⋯S1ⁱ	0.88	2.46	3.3104 (15)	164
N2—H2⋯O1	0.88	2.00	2.6866 (17)	134

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Symmetry code: (i) Inline graphic .

Acknowledgments

MR is grateful to The Quaid-i-Azam University, Islamabad, for financial support for a postdoctoral fellowship.

supplementary crystallographic information

Comment

The background to this study has been set out in our previous work for the structural chemistry of N,N'-disubstituted thiourea (Rauf et al., 2012) and their coordination chemistry. Herein, as a continuation of these crytallographic studies, the structure of the title compound (I) is described, Fig. 1. Compared to N-benzoyl-N'-phenylthioureas [Cambridge Structural Database (Mogul Version 1.7; Allen, 2002], the methyl substitutions at C(10) and C(11)on phenyl ring, implies no significant effect on these bond lengths. and show the molecule to exist in the thione form with typical thiourea C—S and C—O bonds, as well as shortened C—N bond lengths. The dihedral angles to the O(1) C(1) N(1) C(2) N(2)S(1) plane are 79.89 (2)° for the ring formed by C(3) to C(8) and 65.32 (2)° for the ring formed by C(9) to C(14). An intramolecular N—H···O H–bond is present (Table 1), forming a six-membered ring commonly observed in this class of compounds (Rauf et al., 2012). In the crystal packing of (I), intermolecular N—H···S H–bonds link the molecules into centrosymmetric dimers (Fig.2).

Experimental

Freshly prepared 2-chlorobenzoylisothiocyanate (1.98 g, 10 mmol) was dissolved in acetone (30 ml) and stirred for 30 minutes. Afterwards neat 2,3-dimethylaniline(1.21 g, 10 mmol) was added and the resulting mixture was stirred for 2 h. The reaction mixture was then poured into acidified water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ 1,1-dichloromethane (1:1 v/v) to give fine crystals of the title compound (I), with an overall yield of 95% (3.02 g). M.P; 180–181°C Anal. calcd. for C₁₆ H₁₅Cl N₂ O S; C, 60.28 H, 4.74 N, 8.79 S, 10.06 Found: C, 60.22 H, 4.73 N, 8.78 S, 10.01.