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Volume 68 
Part 11 
Page o3099  
November 2012  

Received 1 September 2012
Accepted 5 October 2012
Online 10 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.109
Data-to-parameter ratio = 14.6
Details
Open access

Ethyl 7-methyl-2-((1-methyl-1H-pyrrol-2-yl)methylene)-3-oxo-5-phenyl-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate

aWenzhou Medical College, School of Pharmacy, Wenzhou 325035, People's Republic of China
Correspondence e-mail: proflxk@163.com

In the structure of the title compound, C22H21N3O3S, the thiazole ring forms dihedral angles of 88.83 (7) and 9.39 (9)°, respectively, with the benzene and pyrrole rings. The dihydropyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z conformation.

Related literature

For related structures, see: Hou (2009[Hou, Z.-H. (2009). Acta Cryst. E65, o235.]); 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 thiazolo[3,2-a]pyrimidine derivatives, see: Ashok et al. (2007[Ashok, M., Holla, B. S. & Kumari, N. S. (2007). Eur. J. Med. Chem. 42, 380-385.]); Bahekar & Shinde (2004[Bahekar, S. S. & Shinde, D. B. (2004). Bioorg. Med. Chem. Lett. 14, 1733-1736.]); Hurst & Hull (1961[Hurst, E. W. & Hull, R. (1961). J. Med. Pharm. Chem. 3, 215-229.]); Mehta et al. (2006[Mehta, P. D., Sengar, N. P., Subrahmanyam, E. V. S. & Satyanarayana, D. (2006). Indian J. Pharm. Sci. 68, 103-106.]); Shah & Desai (2007[Shah, T. J. & Desai, V. A. (2007). Arkivoc, 14, 218-228.]); Srivastava et al. (2006[Srivastava, S. K., Jain, A. & Srivastava, S. D. (2006). J. Indian Chem. Soc. 83, 1118-1123.]); Subudhi et al. (2007[Subudhi, B. B., Panda, P. K., Kundu, T., Sahoo, S. & Pradhan, D. (2007). J. Pharm. Res. 6, 114-118.]); Magerramov et al. (2006[Magerramov, A. M., Kurbanova, M. M., Abdinbekova, R. T., Rzaeva, I. A., Farzaliev, V. M. & Allakhverdiev, M. A. (2006). Russ. J. Appl. Chem. 79, 787-790.]); Zhou et al. (2008[Zhou, H., Wu, S., Zhai, S., Liu, A., Sun, Y., Li, R., Zhang, Y., Ekins, S., Swaan, P. W., Fang, B., Zhang, B. & Yan, B. (2008). J. Med. Chem. 51, 1242-1250.]).

[Scheme 1]

Experimental

Crystal data
  • C22H21N3O3S

  • Mr = 407.48

  • Monoclinic, P 21 /n

  • a = 11.8187 (10) Å

  • b = 10.2911 (9) Å

  • c = 16.2290 (14) Å

  • [beta] = 90.584 (2)°

  • V = 1973.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 293 K

  • 0.32 × 0.24 × 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 = 0.814, Tmax = 1.000

  • 10415 measured reflections

  • 3877 independent reflections

  • 3433 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.109

  • S = 1.05

  • 3877 reflections

  • 265 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.19 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: AA2075 ).


Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (grants No. LY12H16003 and Y4110197) and the project of Wenzhou Sci & Tech Bureau (Y20100273). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, is gratefully acknowledged for the data collection.

References

Ashok, M., Holla, B. S. & Kumari, N. S. (2007). Eur. J. Med. Chem. 42, 380-385.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bahekar, S. S. & Shinde, D. B. (2004). Bioorg. Med. Chem. Lett. 14, 1733-1736.  [CrossRef] [PubMed] [ChemPort]
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hou, Z.-H. (2009). Acta Cryst. E65, o235.  [CSD] [CrossRef] [details]
Hurst, E. W. & Hull, R. (1961). J. Med. Pharm. Chem. 3, 215-229.  [CrossRef] [PubMed] [ChemPort]
Magerramov, A. M., Kurbanova, M. M., Abdinbekova, R. T., Rzaeva, I. A., Farzaliev, V. M. & Allakhverdiev, M. A. (2006). Russ. J. Appl. Chem. 79, 787-790.  [ISI] [CrossRef] [ChemPort]
Mehta, P. D., Sengar, N. P., Subrahmanyam, E. V. S. & Satyanarayana, D. (2006). Indian J. Pharm. Sci. 68, 103-106.  [CrossRef] [ChemPort]
Shah, T. J. & Desai, V. A. (2007). Arkivoc, 14, 218-228.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Srivastava, S. K., Jain, A. & Srivastava, S. D. (2006). J. Indian Chem. Soc. 83, 1118-1123.  [ChemPort]
Subudhi, B. B., Panda, P. K., Kundu, T., Sahoo, S. & Pradhan, D. (2007). J. Pharm. Res. 6, 114-118.  [ChemPort]
Zhao, C.-G., Hu, J., Zhang, Y.-L., Zhang, J. & Yang, S.-L. (2011). Acta Cryst. E67, o3009.  [CSD] [CrossRef] [details]
Zhou, H., Wu, S., Zhai, S., Liu, A., Sun, Y., Li, R., Zhang, Y., Ekins, S., Swaan, P. W., Fang, B., Zhang, B. & Yan, B. (2008). J. Med. Chem. 51, 1242-1250.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3099  [ doi:10.1107/S1600536812041748 ]

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