Ethyl 4-[3-(2-methyl­benzo­yl)thio­ureido]benzoate

Aamer Saeed; Hummera Rafique; Amara Mumtaz; Michael Bolte

doi:10.1107/S160053680904183X

. 2009 Oct 17;65(Pt 11):o2774. doi: 10.1107/S160053680904183X

Ethyl 4-[3-(2-methylbenzoyl)thioureido]benzoate

Aamer Saeed ^a,^*, Hummera Rafique ^a, Amara Mumtaz ^a, Michael Bolte ^b

PMCID: PMC2970993 PMID: 21578367

Abstract

The molecular conformation of the title compound, C₁₈H₁₈N₂O₃S, is stabilized by an intramolecular N—H⋯O hydrogen bond. The crystal packing shows centrosymmetric dimers connected by N—H⋯S hydrogen bonds. The terminal ethoxy substituents are statistically disordered [occupancy ratio 0.527 (5):0.473 (5)].

Related literature

For the use of thiourea derivatives in organic synthesis and analysis, see: Eynde & Watte (2003 ▶); Fu et al. (1999 ▶); Rashdan et al. (2006 ▶); Maryanoff et al. (1986 ▶); Wang et al.(2005 ▶); Saeed et al. (2008 ▶); Koch, (2001 ▶). For their bioactivity and pharmaceutical applications, see: Upadhyaya & Srivastava (1982 ▶); Ramadas et al. (1998 ▶); Blum & Hayes (1979 ▶); DeBeer et al. (1936 ▶). For related structures, see: Saeed & Flörke (2007a ▶,b ▶); Saeed et al. (2009 ▶).

Experimental

Crystal data

C₁₈H₁₈N₂O₃S
M _r = 342.40
Triclinic,
a = 7.4555 (3) Å
b = 7.6311 (4) Å
c = 15.2468 (8) Å
α = 96.456 (4)°
β = 103.860 (5)°
γ = 92.908 (4)°
V = 834.13 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.33 × 0.32 × 0.28 mm

Data collection

Stoe IPDS II two-circle-diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T _min = 0.933, T _max = 0.943
22798 measured reflections
4659 independent reflections
4311 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.100
S = 1.04
4659 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 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 global, I. DOI: 10.1107/S160053680904183X/im2145sup1.cif

e-65-o2774-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904183X/im2145Isup2.hkl

e-65-o2774-Isup2.hkl^{(228.2KB, 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—H1⋯O1	0.80	2.01	2.669 (1)	139
N2—H2⋯S1ⁱ	0.89	2.67	3.5551 (9)	170

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

The background of this study has been described in our earlier paper concerning the crystal structure of 1-(2-Chloro-5-nitrophenyl)-3-(2,2-dimethylpropionyl)thiourea (Saeed et al., 2009). As part of our work on the structure of thioureas, we report here the structure of the title derivative, I, Fig 1.

The molecular conformation of the title compound, C₁₈H₁₈N₂O₃S, is stabilized by intramolecular N—H···O hydrogen bonds. The crystal packing shows centrosymmetric dimers connected by N—H···S hydrogen bonds (Table 1). Terminal ethoxy substituents are statistically disordered.

Experimental

A solution of 2-methylbenzoyl chloride (10 mmol) in acetone (50 ml) was added dropwise to a suspension of potassium thiocyanate (10 mmol) in acetone (30 ml) and the reaction mixture was refluxed for 30 min. After cooling to room temperature, a solution of 4-aminobenzoic acid ethyl ester (10 mmol) in acetone (10 ml) was added and the resulting mixture refluxed for 3 h. The reaction mixture was poured into cold water and the precipitated thiourea was recrystallized from aqueous ethanol. Anal. calcd. for C₁₈H₁₈N₂O₃S: C, 63.14; H, 5.30; N, 8.18; S, 9.36% found: C, 63.26; H, 5.34; N, 8.21; S, 9.27%;