N-[(E)-2-Chloro­benzyl­idene]-3-(4-methyl­benzyl­sulfan­yl)-5-(3,4,5-trimethoxy­phen­yl)-4H-1,2,4-triazol-4-amine

Li, Q.-Z.; Song, B.-A.; Yang, S.; Zheng, Y.-G.; Guo, Q.-Q.

doi:10.1107/S1600536809009842

Volume 65
Part 4
Page o869
April 2009

Received 22 February 2009
Accepted 17 March 2009
Online 25 March 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.051
wR = 0.141
Data-to-parameter ratio = 14.3
Details

N-[(E)-2-Chlorobenzylidene]-3-(4-methylbenzylsulfanyl)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-4-amine

Qian-Zhu Li,^a,^b ^* Bao-An Song,^a Song Yang,^a Yu-Guo Zheng ^a and Qing-Qing Guo ^a

^aCenter for Research and Development of Fine Chemicals, Guizhou University, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guiyang 550025, People's Republic of China, and ^bDepartment of Chemistry, Bijie University, Bijie 551700, People's Republic of China
Correspondence e-mail: qianzhuli77@yahoo.com.cn

In the title compound, C₂₆H₂₅ClN₄O₃S, the acyclic imine group exhibits an E configuration. The triazole ring is oriented at dihedral angles of 53.84 (2), 70.77 (1) and 32.59 (3)° with respect to the benzene rings of the 2-chlorobenzylidene, 4-methylbenzylsulfanyl and 3,4,5-trimethoxyphenyl groups, respectively. The crystal packing is stabilized by weak intermolecular C-HN, C-HS and C-H [pi] interactions.

Related literature

For more information on 1,2,4-triazoles, see: He et al. (2006); Kritsanida et al. (2002); Demirbas et al. (2002); Chattopadhyay & Ghosh (1987, 1989).

Experimental

Crystal data

C₂₆H₂₅ClN₄O₃S
M_r = 509.01
Monoclinic, P 2₁ /c
a = 11.283 (4) Å
b = 7.414 (2) Å
c = 31.087 (10) Å
= 100.961 (14)°
V = 2553.1 (14) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 293 K
0.32 × 0.26 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.932, T_max = 0.956
26288 measured reflections
4590 independent reflections
3809 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.141
S = 1.03
4590 reflections
320 parameters
H-atom parameters constrained
_max = 0.50 e Å^-3
_min = -0.65 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C19-H19N4	0.93	2.52	3.000 (3)	112
C10-H10S1	0.93	2.81	3.184 (3)	105
C6-H6N1ⁱ	0.93	2.61	3.409 (3)	144
C8-H8BCg2ⁱⁱ	0.97	2.70	3.427 (2)	133
C24-H24BCg1ⁱⁱⁱ	0.96	2.94	3.588 (2)	125
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) x, y-1, z. Cg1 is the centroid of the C9,C17,N1-N3 ring and Cg2 is the centroid of the C2-C7 ring.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2192 ).

Acknowledgements

The authors acknowledge the National Key Technologies R&D Program of China (2006BAE01A01-13) for supporting this work.

References

Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chattopadhyay, S. K. & Ghosh, S. (1987). Inorg. Chim. Acta, 131, 15-20.
Chattopadhyay, S. K. & Ghosh, S. (1989). Inorg. Chim. Acta, 163, 245-253.
Demirbas, N., Ugurluoglu, R. & Demirbas, A. (2002). Bioorg. Med. Chem. 10, 3717-3723.
He, X., Lu, C. Z., Wu, C. D. & Chen, L. J. (2006). Eur. J. Inorg. Chem., pp. 2491-2503.
Kritsanida, M., Mouroutsou, A., Marakos, P., Pouli, N., Papakonstantinou- Garoufalias, S., Pannecouque, C., Witvrouw, M. & Clercq, E. D. (2002). Farmaco, 57, 253-257.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds