rac-3-{4-[(4-Nitro­benzyl­idene)amino]-3-phenyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenyl­propan-1-one

Wang, W.; Gao, Y.; Xu, C.; Wu, W.; Liu, Q.

doi:10.1107/S1600536811035197

Volume 67
Part 10
Page o2727
October 2011

Received 6 August 2011
Accepted 29 August 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.131
Data-to-parameter ratio = 18.1
Details

rac-3-{4-[(4-Nitrobenzylidene)amino]-3-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl}-1,3-diphenylpropan-1-one

Wei Wang,^a,^b ^* Yan Gao,^b Chao Xu,^b Wen-peng Wu ^b and Qing-lei Liu ^a

^aSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235, People's Republic of China, and ^bSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, People's Republic of China
Correspondence e-mail: zhao_submit@yahoo.com.cn

In the title molecule, C₃₀H₂₃N₅O₃S, the 1,2,4-triazole ring is approximately planar (r.m.s. deviation = 0.006 Å), and forms dihedral angles of 66.0 (2), 65.1 (2), 30.1 (2) and 28.1 (2)° with the four phenyl rings. The phenyl ring of the benzyl group directly attached to the triazole ring is almost perpendicular to the nitrophenyl ring, making a dihedral angle of 84.9 (2)°.

Related literature

For the crystal structures of related 1,2,4-triazole-5(4H)-thione derivatives, see: Al-Tamimi et al. (2010); Fun et al. (2009); Gao et al. (2011); Tan et al. (2010); Wang et al. (2011); Zhao et al. (2010).

Experimental

Crystal data

C₃₀H₂₃N₅O₃S
M_r = 533.59
Monoclinic, P 2₁ /c
a = 13.3303 (13) Å
b = 21.832 (2) Å
c = 9.2773 (9) Å
= 98.213 (3)°
V = 2672.2 (4) Å³
Z = 4
Mo K radiation
= 0.16 mm^-1
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.968, T_max = 0.981
27241 measured reflections
6372 independent reflections
5124 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.131
S = 1.10
6372 reflections
352 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.25 e Å^-3

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ZS2140 ).

Acknowledgements

We gratefully acknowledge support of this study by the Key Laboratory Project of Liaoning Province (No. 2008S127) and the Doctoral Starting Foundation of Liaoning Province (No. 20071103).

References

Al-Tamimi, A.-M. S., Bari, A., Al-Omar, M. A., Alrashood, K. A. & El-Emam, A. A. (2010). Acta Cryst. E66, o1756.
Fun, H.-K., Chantrapromma, S., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o495-o496.
Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794.
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tan, K. W., Maah, M. J. & Ng, S. W. (2010). Acta Cryst. E66, o2224.
Wang, W., Gao, Y., Xiao, Z., Yao, H. & Zhang, J. (2011). Acta Cryst. E67, o269.
Zhao, B., Liu, Z., Gao, Y., Song, B. & Deng, Q. (2010). Acta Cryst. E66, o2814.

organic compounds