(Z)-Ethyl 2-(2,4-dimethyl­benzyl­idene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

Chen, X.-Y.; Wang, H.-C.; Zhang, Q.; Song, Z.-J.; Zheng, F.-Y.

doi:10.1107/S1600536811052925

Volume 68
Part 1
Page o127
January 2012

Received 1 November 2011
Accepted 8 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.050
wR = 0.155
Data-to-parameter ratio = 15.0
Details

(Z)-Ethyl 2-(2,4-dimethylbenzylidene)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate

Xiao-Yan Chen,^a Han-Chu Wang,^a Qian Zhang,^a Zhi-Jian Song ^b and Fei-Yun Zheng ^a ^*

^aThe First Affiliated Hospital, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, and ^bInstitute of Biomedical Informatics/Zhejiang Provincial Key Laboratory of Medical Genetics, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China
Correspondence e-mail: feiyun_zheng@126.com

In the title compound, C₂₅H₂₄N₂O₃S, the dihedral angles between the thiazole ring and the phenyl and substituted benzene rings are 84.91 (11) and 11.58 (10)°, respectively. The dihydropyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z configuration.

Related literature

For related structures, see: Kulakov et al. (2009); Zhao et al. (2011). For background to the biological properties of fused pyrimidine derivatives, see: Al-Rashood & Abdel-Aziz (2010); Ashok et al. (2007); Jang et al. (2011); Wichmann et al. (1999).

Experimental

Crystal data

C₂₅H₂₄N₂O₃S
M_r = 432.52
Monoclinic, P 2₁ /n
a = 9.690 (5) Å
b = 10.620 (5) Å
c = 21.692 (12) Å
= 90.682 (10)°
V = 2232 (2) Å³
Z = 4
Mo K radiation
= 0.17 mm^-1
T = 293 K
0.32 × 0.27 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.675, T_max = 1.000
8761 measured reflections
4257 independent reflections
3096 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.155
S = 1.01
4257 reflections
284 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.26 e Å^-3

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: RN2098 ).

Acknowledgements

The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, is gratefully acknowledged.

References

Al-Rashood, K. A. & Abdel-Aziz, H. A. (2010). Molecules, 15, 3775-3815.
Ashok, M., Holla, B. S. & Kumari, N. S. (2007). Eur. J. Med. Chem. 42, 380-385.
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Jang, M. Y., Lin, Y., De Jonghe, S., Gao, L. J., Vanderhoydonck, B., Froeyen, M., Rozenski, J., Herman, J., Louat, T., Van Belle, K., Waer, M. & Herdewijn, P. (2011). J. Med. Chem. 54, 655-668.
Kulakov, I., Nurkenov, O., Turdybekov, D., Issabaeva, G., Mahmutova, A. & Turdybekov, K. (2009). Chem. Heterocycl. Compd, 45, 856-859.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wichmann, J., Adam, G., Kolczewski, S., Mutel, V. & Woltering, T. (1999). Bioorg. Med. Chem. Lett. 9, 1573-1576.
Zhao, C.-G., Hu, J., Zhang, Y.-L., Zhang, J. & Yang, S.-L. (2011). Acta Cryst. E67, o3009.

organic compounds