3-Acetyl-1-(2-methylphenyl)thiourea

Durre Shahwar; M Nawaz Tahir; Muhammad Mansha Chohan; Naeem Ahmad; M Asam Raza

doi:10.1107/S1600536812011658

. 2012 Mar 24;68(Pt 4):o1160. doi: 10.1107/S1600536812011658

3-Acetyl-1-(2-methylphenyl)thiourea

Durre Shahwar ^a, M Nawaz Tahir ^b,^*, Muhammad Mansha Chohan ^a, Naeem Ahmad ^a, M Asam Raza ^c

PMCID: PMC3344102 PMID: 22606105

Abstract

In the title compound, C₁₀H₁₂N₂OS, the toluene and the N-carbamothioylacetamide units are oriented at dihedral angle of 78.75 (5)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, molecules are linked into [101] chains by pairs of N—H⋯S hydrogen bonds [which generate R ₂ ²(8) loops] and pairs of O—H⋯O hydrogen bonds [which generate R ₂ ²(4) loops]. The two motifs alternate in the chain.

Related literature

For related structures, see: Shahwar et al. (2012 ▶). For graph–set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₀H₁₂N₂OS
M _r = 208.28
Monoclinic,
a = 5.0444 (2) Å
b = 20.7019 (9) Å
c = 9.9464 (4) Å
β = 95.116 (2)°
V = 1034.55 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.35 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.915, T _max = 0.938
7696 measured reflections
1812 independent reflections
1512 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.088
S = 1.17
1812 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011658/hb6692sup1.cif

e-68-o1160-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011658/hb6692Isup2.hkl

e-68-o1160-Isup2.hkl^{(87.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812011658/hb6692Isup3.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⋯O1	0.86	1.99	2.664 (2)	135
N1—H1⋯O1ⁱ	0.86	2.50	3.172 (2)	135
N2—H2⋯S1ⁱⁱ	0.86	2.52	3.3747 (17)	171

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. They also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The title compound I (Fig. 1) has been synthesized in continuation of our efforts to find new enzyme inhibitors.

The crystal structures of N-(phenylcarbamothioyl)acetamide (Shahwar et al., 2012) has been published which is related to the title compound (I).

In (I), the toluene group A (C1–C7) and the N-carbamothioylacetamide moiety B (N1/C8/S1/N2/C9/O1/C10) are planar with r. m. s. deviation of 0.0058 Å and 0.0278 Å, respectively. The dihedral angle between A/B is 78.75 (5)°. There exist classical intramolecular H–bonding of N—H···O type (Table 1, Fig. 1) with S(6) ring motif (Bernstein et al., 1995). The molecules are dimerized due to N—H···S type of hydrogen bonds with R₂²(8) ring motifs (Table 1, Fig. 2). The dimers are interlinked from S(6) ring motifs due to strong N—H···O H–bondings (Table 1, Fig. 2) with centrosymmetric four membered ring motif (—O···H···O···H···O—) (Table 1, Fig. 2). The polymeric chains extend along the base vector [101].

Experimental

The title compound (I) was synthesized by adding (0.1 mol, 7.13 ml) of acetylchloride dropwise to a stirred solution of KSCN (0.11 mol) in dry acetone (50 ml), followed by slow addition of toluidine (0.1 mol) in dry acetone (25 ml). The mixture was refluxed for 5–10 min, then poured on ice cooled water, which resulted in crude precipitate. Recrystallization of the precipitate in ethylacetate yielded colourless needles.