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

Pawar, S.; Bhatt, P.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536811052585

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 (C-C) = 0.003 Å
R = 0.035
wR = 0.084
Data-to-parameter ratio = 18.9
Details

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

Sunayna Pawar,^a Pralav Bhatt,^b Thavendran Govender,^a Hendrik G. Kruger ^b and Glenn E. M. Maguire ^b ^*

^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-HN 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); Kawthekar et al. (2010); Peters et al. (2010); Naicker et al. (2010). For related structures, see: Naicker et al. (2011a,b).

Experimental

Crystal data

C₁₈H₁₆N₂S
M_r = 292.39
Trigonal, P 3₂
a = 16.223 (1) Å
c = 4.8130 (3) Å
V = 1097.0 (1) Å³
Z = 3
Mo K radiation
= 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) T_min = 0.958, T_max = 0.981
14735 measured reflections
3676 independent reflections
3205 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(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
_max = 0.23 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), 1832 Friedel pairs
Flack parameter: -0.02 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11N1ⁱ	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); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); 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.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011a). Acta Cryst. E67, o67.
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011b). Acta Cryst. E67, o1403.
Naicker, T., Petzold, K., Singh, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 2859-2867.
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.

organic compounds