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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 [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.155
Data-to-parameter ratio = 15.0
Details
Open access

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

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[Kulakov, I., Nurkenov, O., Turdybekov, D., Issabaeva, G., Mahmutova, A. & Turdybekov, K. (2009). Chem. Heterocycl. Compd, 45, 856-859.]); Zhao et al. (2011[Zhao, C.-G., Hu, J., Zhang, Y.-L., Zhang, J. & Yang, S.-L. (2011). Acta Cryst. E67, o3009.]). For background to the biological properties of fused pyrimidine derivatives, see: Al-Rashood & Abdel-Aziz (2010[Al-Rashood, K. A. & Abdel-Aziz, H. A. (2010). Molecules, 15, 3775-3815.]); Ashok et al. (2007[Ashok, M., Holla, B. S. & Kumari, N. S. (2007). Eur. J. Med. Chem. 42, 380-385.]); Jang et al. (2011[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.]); Wichmann et al. (1999[Wichmann, J., Adam, G., Kolczewski, S., Mutel, V. & Woltering, T. (1999). Bioorg. Med. Chem. Lett. 9, 1573-1576.]).

[Scheme 1]

Experimental

Crystal data
  • C25H24N2O3S

  • Mr = 432.52

  • Monoclinic, P 21 /n

  • a = 9.690 (5) Å

  • b = 10.620 (5) Å

  • c = 21.692 (12) Å

  • [beta] = 90.682 (10)°

  • V = 2232 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.675, Tmax = 1.000

  • 8761 measured reflections

  • 4257 independent reflections

  • 3096 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.155

  • S = 1.01

  • 4257 reflections

  • 284 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ChemPort] [PubMed]
Ashok, M., Holla, B. S. & Kumari, N. S. (2007). Eur. J. Med. Chem. 42, 380-385.  [ISI] [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [PubMed]
Kulakov, I., Nurkenov, O., Turdybekov, D., Issabaeva, G., Mahmutova, A. & Turdybekov, K. (2009). Chem. Heterocycl. Compd, 45, 856-859.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wichmann, J., Adam, G., Kolczewski, S., Mutel, V. & Woltering, T. (1999). Bioorg. Med. Chem. Lett. 9, 1573-1576.  [CrossRef] [PubMed] [ChemPort]
Zhao, C.-G., Hu, J., Zhang, Y.-L., Zhang, J. & Yang, S.-L. (2011). Acta Cryst. E67, o3009.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o127  [ doi:10.1107/S1600536811052925 ]

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