N-(5-Chloro-3-methyl-1-phenyl­pyrazol-4-ylcarbon­yl)-N′-(2-methoxy­phen­yl)thio­urea

Du, H.; Du, H.; Lu, M.; Sun, L.

doi:10.1107/S1600536807068390

Volume 64
Part 3
Page o609
March 2008

Received 17 November 2007
Accepted 25 December 2007
Online 20 February 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.035
wR = 0.098
Data-to-parameter ratio = 14.9
Details

N-(5-Chloro-3-methyl-1-phenylpyrazol-4-ylcarbonyl)-N'-(2-methoxyphenyl)thiourea

Hai-tang Du,^a ^* Hai-jun Du,^b Ming Lu ^c and Li-li Sun ^d

^aDepartment of Biology and Environmental Technology, Guiyang College, Guiyang 550005, People's Republic of China,^bSchool of Chemistry and Environmental Science, Guizhou University for Nationalites, Guiyang 550025, People's Republic of China,^cSchool of Computer Science and Technology, Tianjin University, Tianjin 300072, People's Republic of China, and ^dDepartment of Chemistry, Tianjin University, Tianjin 300072, People's Republic of China
Correspondence e-mail: haitangdu@sohu.com

In the title compound, C₁₉H₁₇ClN₄O₂S, the dihedral angle between the pyrazole and phenyl rings is 43.3 (3)°. The bridging unit between the pyrazole and methoxyphenyl rings is planar within 0.0169 Å and makes dihedral angles of 2.3 and 26.4°, respectively, with these two rings. This conformation is influenced by intramolecular N-HO and N-HCl hydrogen bonds. The crystal packing is stabilized by C-H [pi] interactions.

Related literature

For related literature, see: Du et al. (2007); Saeed & Flörke (2007); Wang et al. (2007).

Experimental

Crystal data

C₁₉H₁₇ClN₄O₂S
M_r = 400.88
Monoclinic, P 2₁ /c
a = 20.339 (2) Å
b = 7.4408 (9) Å
c = 12.7919 (15) Å
= 107.029 (2)°
V = 1851.0 (4) Å³
Z = 4
Mo K radiation
= 0.34 mm^-1
T = 294 (2) K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.922, T_max = 0.941
10087 measured reflections
3793 independent reflections
3065 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.097
S = 1.04
3793 reflections
254 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C13-C18 rings, respectively.

D-HA	D-H	HA	DA	D-HA
N3-H3ACl1	0.890 (9)	2.398 (14)	3.1657 (14)	144.6 (17)
N4-H4AO1	0.895 (9)	1.913 (15)	2.6589 (19)	139.6 (18)
C2-H2Cg1ⁱ	0.93	2.88	3.613 (2)	136
C10-H10BCg2ⁱⁱ	0.96	2.98	3.809 (2)	146
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2053 ).

Acknowledgements

The authors thank Guiyang College (grant No. 2007012) for financial support.

References

Bruker (1997). SMART (Version 5.611) and SAINT (Version 6.0). Bruker AXS Inc., Madison, Wisconsin, USA.
Du, H.-T., Lu, M., Zhou, W.-Y. & Sun, L.-L. (2007). Acta Cryst. E63, o4287.
Saeed, A. & Flörke, U. (2007). Acta Cryst. E63, o3695.
Sheldrick, G. M. (1996). SADABS. Version 2.03. University of Göttingen, Germany.
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Wang, J., Tian, L. & Liu, S.-Y. (2007). Acta Cryst. E63, o3667.

organic compounds