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Volume 69 
Part 6 
Page o898  
June 2013  

Received 27 April 2013
Accepted 9 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.149
Data-to-parameter ratio = 18.7
Details
Open access

8,11,24-Trioxa-21-thia-19-azapentacyclo[16.6.0.02,7.012,17.019,23]tetracosa-2(7),3,5,12,14,16-hexaene

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C19H19NO3S, the thiazole and oxazolidine rings each adopt an envelope conformation, with the S and O atoms as the respective flap atoms. The thiazole and oxazolidine rings (all atoms) make a dihedral angle of 66.39 (11)° while the phenyl rings subtend a dihedral angle of 22.71 (10)°.

Related literature

For the biological activity of thiazole derivatives, see: Guo et al. (2006[Guo, C. B., Guo, Y. S., Guo, Z. R., Xiao, J. F., Chu, F. M. & Cheng, G. F. (2006). Acta Chim. Sin. 64, 1559-1564.]); Karegoudar et al. (2008[Karegoudar, P., Karthikeyan, M. S., Prasad, D. J., Mahalinga, M., Holla, B. S. & Kumari, N. S. (2008). Eur. J. Med. Chem. 43, 261-267.]); Reddy et al. (1999[Reddy, K. A., Lohray, B. B., Bhushan, V., Bajji, A. C., Reddy, K. V., Reddy, P. R., Krishna, T. H., Rao, I. N. & Jajoo, H. K. (1999). J. Med. Chem. 42, 1927-1940.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19NO3S

  • Mr = 341.42

  • Monoclinic, P 21 /c

  • a = 10.725 (5) Å

  • b = 10.405 (5) Å

  • c = 14.930 (5) Å

  • [beta] = 100.262 (5)°

  • V = 1639.4 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.938, Tmax = 0.958

  • 15331 measured reflections

  • 4067 independent reflections

  • 2586 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.149

  • S = 1.03

  • 4067 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6902 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SK,TS and DV acknowlege the UGC (SAP-CAS) for the departmental facilties. SK thanks the DST PURSE for a Junior Research Fellowship and TS thanks the DST Inspire for a fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Guo, C. B., Guo, Y. S., Guo, Z. R., Xiao, J. F., Chu, F. M. & Cheng, G. F. (2006). Acta Chim. Sin. 64, 1559-1564.  [ChemPort]
Karegoudar, P., Karthikeyan, M. S., Prasad, D. J., Mahalinga, M., Holla, B. S. & Kumari, N. S. (2008). Eur. J. Med. Chem. 43, 261-267.  [ISI] [CrossRef] [PubMed] [ChemPort]
Reddy, K. A., Lohray, B. B., Bhushan, V., Bajji, A. C., Reddy, K. V., Reddy, P. R., Krishna, T. H., Rao, I. N. & Jajoo, H. K. (1999). J. Med. Chem. 42, 1927-1940.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o898  [ doi:10.1107/S1600536813012798 ]

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