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Volume 68 
Part 1 
Page o176  
January 2012  

Received 7 September 2011
Accepted 6 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.084
Data-to-parameter ratio = 18.9
Details
Open access

(S)-4-Phenyl-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)-1,3-thiazole

aSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa, and bSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
Correspondence e-mail: maguireg@ukzn.ac.za

In the title compound, C18H16N2S, the N-containing ring adopts a half-chair configuration. The crystal packing features C-H...N contacts. There is no [pi]-[pi] stacking within the crystal structure.

Related literature

The title compound is a potential ligand for the asymmetric Henry reaction. For the application of these ligands as catalysts, see: Chakka et al. (2010[Chakka, S. K., Peters, B. K., Andersson, P. G., Maguire, G. E. M., Kruger, H. G. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 2295-2301.]); Kawthekar et al. (2010[Kawthekar, R. B., Chakka, S. K., Francis, V., Andersson, P. G., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 846-852.]); Peters et al. (2010[Peters, B. K., Chakka, S. K., Naicker, T., Maguire, G. E. M., Kruger, H. G., Andersson, P. G. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 679-, 687.]); Naicker et al. (2010[Naicker, T., Petzold, K., Singh, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 2859-2867.]). For related structures, see: Naicker et al. (2011a[Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011a). Acta Cryst. E67, o67.],b[Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011b). Acta Cryst. E67, o1403.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16N2S

  • Mr = 292.39

  • Trigonal, P 32

  • a = 16.223 (1) Å

  • c = 4.8130 (3) Å

  • V = 1097.0 (1) Å3

  • Z = 3

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 173 K

  • 0.20 × 0.10 × 0.09 mm

Data collection
  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.958, Tmax = 0.981

  • 14735 measured reflections

  • 3676 independent reflections

  • 3205 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.084

  • S = 1.03

  • 3676 reflections

  • 194 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1832 Friedel pairs

  • Flack parameter: -0.02 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...N1i 0.95 2.54 3.341 (3) 142
Symmetry code: (i) [-y+1, x-y+2, z-{\script{1\over 3}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2110 ).


Acknowledgements

The authors thank Dr Hong Su of the University of Capetown for the data collection and structure refinement.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakka, S. K., Peters, B. K., Andersson, P. G., Maguire, G. E. M., Kruger, H. G. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 2295-2301.  [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Kawthekar, R. B., Chakka, S. K., Francis, V., Andersson, P. G., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 846-852.  [CrossRef] [ChemPort]
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011a). Acta Cryst. E67, o67.  [CrossRef] [details]
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011b). Acta Cryst. E67, o1403.  [CSD] [CrossRef] [details]
Naicker, T., Petzold, K., Singh, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 2859-2867.  [ISI] [CrossRef] [ChemPort]
Peters, B. K., Chakka, S. K., Naicker, T., Maguire, G. E. M., Kruger, H. G., Andersson, P. G. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 679-, 687.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o176  [ doi:10.1107/S1600536811052585 ]

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