[Journal logo]

Volume 69 
Part 6 
Page o892  
June 2013  

Received 2 May 2013
Accepted 9 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.152
Data-to-parameter ratio = 33.1
Details
Open access

8,13,26-Trioxa-23-thia-21-azapentacyclo[18.6.0.02,7.014,19.021,25]hexacosa-2(7),3,5,14,16,18-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, C21H23NO3S, both the thiazole and oxazolidine rings adopt twist conformations. The mean plane of the thiazole ring makes a dihedral angle of 61.02 (7)° with the oxazolidine ring mean plane, and dihedral angles of 22.72 (6) and 75.07 (6)° with the benzene rings. The benzene rings are almost perpendicular to one another, making a dihedral angle of 89.14 (6)°. There are bifurcated intramolecular C-H...O hydrogen bonds in the molecular structure. In the crystal, molecules are linked via C-H...[pi] interactions, forming chains propagating along [100].

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
  • C21H23NO3S

  • Mr = 369.46

  • Monoclinic, P 21 /c

  • a = 9.9858 (5) Å

  • b = 17.8830 (8) Å

  • c = 10.2054 (4) Å

  • [beta] = 94.663 (2)°

  • V = 1816.41 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 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 = 0.943, Tmax = 0.961

  • 29183 measured reflections

  • 7768 independent reflections

  • 5150 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.152

  • S = 1.02

  • 7768 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9-C14 ring.

D-H...A D-H H...A D...A D-H...A
C8-H8...O1 0.98 2.30 2.9593 (13) 123
C8-H8...O2 0.98 2.30 2.7146 (14) 104
C3-H3...Cg1i 0.93 2.99 3.8672 (14) 158
C16-H16B...Cg1ii 0.97 2.81 3.7400 (17) 160
Symmetry codes: (i) x-1, y, z; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

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: SU2596 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India for data collection. SK, TS and DV the UGC (SAP-CAS) for the departmental facilities. 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, o892  [ doi:10.1107/S1600536813012804 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.