N-(3-Chloro-4-eth­oxy­benzo­yl)-N′-(2-meth­oxy­phen­yl)thio­urea

Jing-Han Hu; Zhong-Yi Luo; Chen-Fei Ding; Xiao-Li Song

doi:10.1107/S1600536810054644

. 2011 Jan 12;67(Pt 2):o376. doi: 10.1107/S1600536810054644

N-(3-Chloro-4-ethoxybenzoyl)-N′-(2-methoxyphenyl)thiourea

Jing-Han Hu ^a,^*, Zhong-Yi Luo ^a, Chen-Fei Ding ^a, Xiao-Li Song ^a

PMCID: PMC3051694 PMID: 21523053

Abstract

In the title compound, C₁₇H₁₇ClN₂O₃S, the central carbonylthiourea unit is nearly planar [maximum atomic deviation = 0.019 (3) Å] and makes dihedral angles of 2.47 (7) and 17.76 (6)° with the terminal benzene rings. An intramolecular N—H⋯O hydrogen bond occurs. Weak intermolecular C—H⋯S and C—H⋯Cl hydrogen bonding is observed in the crystal structure.

Related literature

For applications of thiourea derivatives, see: Antholine & Taketa (1982 ▶); Schroeder (1955 ▶). For related structures, see: Yusof & Yamin (2004a ▶,b ▶); Ali et al. (2004 ▶). For related acylthiourea derivatives, see: Zhang et al. (2003 ▶, 2006 ▶).

Experimental

Crystal data

C₁₇H₁₇ClN₂O₃S
M _r = 364.84
Triclinic,
a = 7.8238 (8) Å
b = 8.4791 (11) Å
c = 14.9867 (13) Å
α = 76.365 (7)°
β = 89.384 (5)°
γ = 62.647 (4)°
V = 852.65 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.38 × 0.35 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.874, T _max = 0.908
4903 measured reflections
3314 independent reflections
2679 reflections with I > 2σ(I)
R _int = 0.012

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.216
S = 1.06
3314 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054644/xu5125sup1.cif

e-67-0o376-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054644/xu5125Isup2.hkl

e-67-0o376-Isup2.hkl^{(162.5KB, 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⋯O2	0.86	1.88	2.613 (3)	143
C6—H6⋯S1ⁱ	0.93	2.86	3.468 (2)	124
C14—H14⋯Cl1ⁱⁱ	0.93	2.81	3.680 (3)	156

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

Acknowledgments

We acknowledge the support of the Colleges and Universities Graduate Advisor Research Project in Gansu Province, China (No. 0804–11)

supplementary crystallographic information

Comment

Thiourea derivatives have been studied for their potential use in agriculture, medicine and analytical chemistry (Schroeder, 1955; Antholine & Taketa, 1982). As part of our ongoing work on acylthiourea derivatives (Zhang et al., 2003; Zhang et al., 2006), we present here the structure of the title thiourea derivative, (I).

Benzoylthiourea derivatives can be synthesized from the reaction between benzoylisothiocyanate and amine compounds. In the title compound, (I), the molecular structure and dimensions are similar to those in other benzoylthiourea derivatives, such as N-(2-chlorophenyl)-N'-(4-methoxybenzoyl)thiourea (Yusof & Yamin, 2004a), N-(4-methoxybenzoyl-N'-(o-tolyl)thiourea (Yusof & Yamin, 2004b) and N-(p-methoxybenzoyl)-N'-(o-methoxyphenyl)thiourea (Ali et al., 2004). The molecule maintains its trans-cis configuration with respect to the position of the 3-chloro-4-ethoxybenzoyl and 2-methoxyphenyl groups relative to the S atom across the thiourea C—N bonds.

The central carbonyl thiourea moiety (S1/O2/N1/N2/C9/C10), the 2-methoxyphenyl group (C11–C16/O3/C23) and the 3-chloro-4-ethoxybenzoyl (C1–C6/C8/O1) group are individually planar. The C10—S1, C10—N1 and C10—N2 bond lengths are1.665 (2), 1.392 (2) and 1.333 (3) Å, respectively, comparable with those in N-(2-chlorophenyl)-N'- (4-methoxybenzoyl)-thiourea [C═S = 1.662 (2) Å, C8—N1 = 1.386 (3) Å and C8—N2 = 1.331 (3) Å; Yusof & Yamin, 2004a] and other benzoylthiourea derivatives. There is one intramolecular hydrogen bonds, via N2—H2···O2; as a result, one pseudo-six-membered rings, is formed (Fig. 1).

Experimental

Potassium thiocyanate (7.5 mmol), 3-chloro-4-ethoxybenzoyl chloride (5 mmol), PEG-400 (3% with respect to ammonium thiocyanate) and dichloromethane (20 ml) were placed in a dried flask and stirred at room temperature for 1 h, then 2-methoxyaniline (5 mmol) was added. The mixture was stirred for 0.5 h at room temperature and a precipitate was formed. This was filtered off, washed with water and dried. yellow single crystals of (I) were obtained from an ethanol–dimethylformamide (1:1) solution.