N-(2-Chloro­benzo­yl)-N′-(3-pyrid­yl)thio­urea

Chai, L.-Q.; Ding, Y.-J.; Yang, X.-Q.; Yan, H.-B.; Dong, W.-K.

doi:10.1107/S1600536808019922

Volume 64
Part 8
Page o1407
August 2008

Received 14 June 2008
Accepted 30 June 2008
Online 5 July 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.037
wR = 0.100
Data-to-parameter ratio = 13.5
Details

N-(2-Chlorobenzoyl)-N'-(3-pyridyl)thiourea

Lan-Qin Chai,^a Yu-Jie Ding,^b Xiao-Qing Yang,^a Hai-Bo Yan ^a and Wen-Kui Dong ^a ^*

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bDepartment of Biochemical Engineering, Anhui University of Technology and Science, Wuhu 241000, People's Republic of China
Correspondence e-mail: dongwk@mail.lzjtu.cn

In the molecule of the title compound, C₁₃H₁₀ClN₃OS, the dihedral angles between the plane through the thiourea group and the pyridine and benzene rings are 53.08 (3) and 87.12 (3)°, respectively. The molecules are linked by intermolecular N-HN hydrogen-bonding interactions to form a supramolecular chain structure along the a axis. An intramolecular N-HO hydrogen bond is also present.

Related literature

For related literature, see: Campo et al. (2002); Dong et al. (2006, 2008); Foss et al. (2004); Guillon et al. (1996); Koch (2001); Krepps et al. (2001); Su et al. (2004, 2006); Teoh et al. (1999); Venkatachalam et al. (2004); West et al. (2000); Xian et al. (2004).

Experimental

Crystal data

C₁₃H₁₀ClN₃OS
M_r = 291.75
Triclinic, $[P \overline 1]$
a = 8.421 (3) Å
b = 9.282 (4) Å
c = 10.512 (4) Å
= 98.336 (4)°
= 110.797 (4)°
= 112.532 (4)°
V = 670.9 (5) Å³
Z = 2
Mo K radiation
= 0.43 mm^-1
T = 298 (2) K
0.32 × 0.11 × 0.07 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.874, T_max = 0.972
3504 measured reflections
2319 independent reflections
1734 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.100
S = 1.02
2319 reflections
172 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1	0.86	1.98	2.671 (3)	137
N1-H1N3ⁱ	0.86	2.08	2.886 (4)	157
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2227 ).

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604-01) and the 'Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03-01 A), which are gratefully acknowledged.

References

Campo, R., Criado, J. J. & Garcia, E. (2002). J. Inorg. Biochem. 89, 74-82.
Dong, W. K., Yang, X. Q., Chai, L. Q., Tian, Y. Q. & Feng, J. H. (2008). Phosphorus Sulfur Silicon, 183, 1181-1187.
Dong, W.-K., Yang, X.-Q. & Feng, J.-H. (2006). Acta Cryst. E62, o3459-o3460.
Foss, O., Husebye, S., Törnroos, K. W. & Fanwick, P. E. (2004). Polyhedron, 23, 3021-3032.
Guillon, E., Mohamadou, G. & Déchamps-Olivier, I. (1996). Polyhedron, 15, 947-952.
Koch, K. R. (2001). Coord. Chem. Rev. 216-217, 473-488.
Krepps, M. K., Parkin, S. & Atwood, D. A. (2001). Cryst. Growth Des. 1, 291-297.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Su, B. Q., Liu, G. L. & Sheng, L. (2006). Phosphorus Sulfur Silicon, 181, 745-750.
Su, B.-Q., Xian, L., Song, H.-B. & Sheng, L. (2004). Acta Cryst. C60, m661-m662.
Teoh, S. G., Ang, S. H. & Fun, H. K. (1999). J. Organomet. Chem. 580, 17-21.
Venkatachalam, T. K., Sudbeck, E. & Uckun, F. M. (2004). J. Mol. Struct. 687, 45-51.
West, D. X., Castiñeiras, A. & Bermejo, E. (2000). J. Mol. Struct. 520, 103-106.
Xian, L., Wei, T. B. & Zhang, Y. M. (2004). J. Coord. Chem. 57, 453-457.

organic compounds