N-[(2,4-Dimethyl­phen­yl)carbamothio­yl]-2-methyl­benzamide

B M Yamin; S Yousuf; M S M Yusof; R H Jusoh

doi:10.1107/S1600536808009501

. 2008 Apr 10;64(Pt 5):o832. doi: 10.1107/S1600536808009501

N-[(2,4-Dimethylphenyl)carbamothioyl]-2-methylbenzamide

B M Yamin ^a, S Yousuf ^b,^*, M S M Yusof ^c, R H Jusoh ^c

PMCID: PMC2961187 PMID: 21202321

Abstract

The title compound, C₁₇H₁₈N₂OS, adopts a trans–cis geometry of the thiourea group which is stabilized by intramolecular hydrogen bonds between the O atom of the carbonyl group and the H atom of the thioamide group. A C—H⋯S intramolecular hydrogen bond is also present. In the crystal structure, molecules are linked by intermolecular N—H⋯S hydrogen bonds to form centrosymmetric dimers.

Related literature

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

Experimental

Crystal data

C₁₇H₁₈N₂OS
M _r = 298.39
Triclinic,
a = 6.2569 (15) Å
b = 9.862 (2) Å
c = 13.986 (3) Å
α = 69.461 (4)°
β = 86.199 (4)°
γ = 75.206 (4)°
V = 781.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 298 (2) K
0.27 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.946, T _max = 0.982
7817 measured reflections
2904 independent reflections
2069 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.119
S = 1.02
2904 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 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/S1600536808009501/at2557sup1.cif

e-64-0o832-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009501/at2557Isup2.hkl

e-64-0o832-Isup2.hkl^{(142.5KB, 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	2.03	2.706	135
C17—H17B⋯S1	0.96	2.80	3.496	130
N1—H1⋯S1ⁱ	0.86	2.57	3.372	155

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Ministry of Higher Education of Malaysia for Fundamental Research Grants OUP UKM-OUP-BIT-28/20076 and UMT-FRGS-59001, and Universiti Kebangsaan Malaysia and HEJ Research Institute of Chemistry, University of Karachi, for research facilities.

supplementary crystallographic information

Comment

The title compound, (I), is isomeric to the previously reported 1-(2,3-dimethylphenyl)-3-(2-methylbenzoyl)thiourea (II), (Khawar Rauf et al., 2007) with the difference that the 2,3-dimethylphenyl ring is replaced by 2,4-dimethylphenyl (Fig.1). The bond lengths and angles are in normal range (Allen et al., 1987) and in agreement with those in (II). The central thiourea moiety (S1/N1/N2/C9), 2-methylbenzoyl (C1—C8), and 2,3-dimethylphenyl (C10—C15) rings are each planar with a maximum deviation of 0.040 (2)Å for C8 atom from the least square plane. The dihedral angles between the thiourea moiety and the 2-methylbenzoyl and 2,3-dimethylphenyl rings are 52.96 (11) and 70.34 (12)°, respectively. The trans-cis geometry of the thiourea moiety is stabilized by N2—H2···O1 and C17—H17B···S1 intramolecular hydrogen bonds. In the crystal structure, the molecules are linked to form dimers by the N1—H1···S1 intermolecular hydrogen bond (symmtery codes as in Table 2) and arranged parallel to c axis (Fig.2).

Experimental

The mixture of 2-methylbenzoyl chloride (9.720 g, 0.025 mol) with the equimolar amount of ammonium thiocyanate (1.903 g, 0.025 mol) and 2,3-dimethyl aniline (3.025 g, 0.025 mol) in 40 ml dry acetone was refluxed with stirring for 4 h. The solution was filtered and left to evaporate at room temperature. The colourless crystals obtained after a few days, was found suitable for X-ray investigations. The yield was 85% with melting point 413.2–415.7 K.