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

Hu, J.-H.; Luo, Z.-Y.; Ding, C.-F.; Song, X.-L.

doi:10.1107/S1600536810054644

Volume 67
Part 2
Page o376
February 2011

Received 16 December 2010
Accepted 29 December 2010
Online 12 January 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.061
wR = 0.216
Data-to-parameter ratio = 15.1
Details

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

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

^aCollege of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
Correspondence e-mail: hujinghan62@163.com

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-HO hydrogen bond occurs. Weak intermolecular C-HS and C-HCl 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, $[P \overline 1]$
a = 7.8238 (8) Å
b = 8.4791 (11) Å
c = 14.9867 (13) Å
= 76.365 (7)°
= 89.384 (5)°
= 62.647 (4)°
V = 852.65 (16) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.012

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.216
S = 1.06
3314 reflections
219 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.85 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O2	0.86	1.88	2.613 (3)	143
C6-H6S1ⁱ	0.93	2.86	3.468 (2)	124
C14-H14Cl1ⁱⁱ	0.93	2.81	3.680 (3)	156
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y+1, z-1.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: XU5125 ).

Acknowledgements

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

References

Ali, H., Halim, S. N. A., Khamis, N. A., Yusof, M. S. & Yamin, B. M. (2004). Acta Cryst. E60, o1497-o1498.
Antholine, W. & Taketa, F. (1982). J. Inorg. Biochem. 16, 145-154.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Schroeder, D. C. (1955). Chem. Rev. 50, 181-228.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yusof, M. S. M. & Yamin, B. M. (2004a). Acta Cryst. E60, o1998-o1999.
Yusof, M. S. M. & Yamin, B. M. (2004b). Acta Cryst. E60, o1687-o1688.
Zhang, Y.-M., Cao, C., Lin, Q. & Wei, T.-B. (2006). Acta Cryst. E62, o1791-o1792.
Zhang, Y.-M., Xian, L. & Wei, T.-B. (2003). Acta Cryst. C59, m473-m474.

organic compounds