1-(2-Methyl­benzo­yl)-3-m-tolyl­thio­urea

B M Yamin; S Yousuf; M S M Yusof; T N D T Zakaria

doi:10.1107/S1600536808012300

. 2008 Jun 7;64(Pt 7):o1227. doi: 10.1107/S1600536808012300

1-(2-Methylbenzoyl)-3-m-tolylthiourea

B M Yamin ^a, S Yousuf ^b,^*, M S M Yusof ^c, T N D T Zakaria ^c

PMCID: PMC2961788 PMID: 21202864

Abstract

The molecule of the title compound, C₁₆H₁₆N₂OS, is not planar; the two aromatic rings are inclined to one another by 37.59 (9)°. There are intramolecular hydrogen bonds between the benzoyl O atom and the H atom of the thioamide N atom, and between the thiourea S atom and the H atom of the tolyl group. These hydrogen bonds stabilize the molecule in such a way that the thiourea group adopts a trans–cis geometry. In the crystal structure, molecules are linked by N—H⋯S intermolecular hydrogen bonds, forming centrosymmetric dimers.

Related literature

For the crystal structure of 1-(2,3-dimethylphenyl)-3-(2-methylbenzoyl)thiourea, see: Khawar Rauf et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂OS
M _r = 284.37
Triclinic,
a = 6.440 (3) Å
b = 10.201 (5) Å
c = 11.415 (5) Å
α = 77.310 (7)°
β = 89.896 (8)°
γ = 86.468 (8)°
V = 730.1 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.35 × 0.34 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.927, T _max = 0.954
7240 measured reflections
2703 independent reflections
2202 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.125
S = 1.02
2703 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012300/su2052sup1.cif

e-64-o1227-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012300/su2052Isup2.hkl

e-64-o1227-Isup2.hkl^{(132.7KB, 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—H1A⋯S1ⁱ	0.86	2.74	3.407 (2)	136
N2—H2A⋯O1	0.86	1.97	2.658 (2)	136
C7—H7C⋯O1	0.96	2.52	2.933 (3)	106
C15—H15A⋯S1	0.93	2.54	3.168 (3)	125

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Ministry of Higher Education of Malaysia for the Fundamental Research Grants UKM-OUP-BTT-28–2007 and UMT-FRGS-59001, and University Kebangsaan Malaysia, University Malaysia Terengganuand and the HEJ Research Institute of Chemistry, University of Karachi, for research facilities.

supplementary crystallographic information

Comment

The title compound, (I), is analogus to 1-(2,3-Dimethylphenyl)-3-(2-methylbenzoyl)thiourea (II) (Khawar Rauf et al., 2007), but with the 2,3-dimethyl phenyl group replaced by a 2-methyl phenyl (m-tolyl) group (Fig. 1). The molecule maintains the trans-cis configuration with respect to the position of the methyl benzoyl and 3-methyl benzene groups, respectively, relative to the thiono S1 atom. The bond lengths and angles are in normal ranges (Allen et al., 1987). The central thiourea moiety, S1/N1/N2/C9, the 2-methylbenzoyl ring, (C1—C8), and the m-tolyl group (C10—C15,C16) are all relatively planar, with a maximum deviation from any best mean plane of 0.015 (2) Å for atom C10. The central thiourea moiety makes dihedral angles with the 2-methylbenzoyl and m-tolyl fragments of 49.61 (7) and 17.87 (9)°, respectively. The trans-cis geometry of the thiourea moiety is stabilized by N2—H2A···O1, C7—H7C···O1 and C15—H15A···S1 intramolecular hydrogen bonds (Table 1).

In the crystal structure of (I), symmetry related molecules are linked by the N1—H1A···S1 intermolecular hydrogen bonds (Table 1) to form cenntrosymmetric dimers (Fig 2).

Experimental

2-methylbenzoyl chloride (9.720 g, 0.025mole) was mixed with an equimolar amount of ammonium thiocyanate (1.903 g, 0.025 mol) and 3-methyl aniline (2.701 g, 0.025 mol) in 45 ml dry acetone. The mixture was refluxed with stirring for 4 h. The solution was then filtered and left to evaporate at room temperature. Colourless crystals, suitable for X-ray aanalysis, were obtained after a few days (Yield 85%).