5-Chloro-4′-ethyl-3H-spiro­[1,3-benzo­thia­zole-2,1′-cyclo­hexa­ne]

Akkurt, M.; Cihan-Üstündağ, G.; Çapan, G.; Türktekin-Çelikesir, S.; Tahir, M.N.

doi:10.1107/S1600536812016479

Volume 68
Part 5
Page o1466
May 2012

Received 14 April 2012
Accepted 16 April 2012
Online 21 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.038
wR = 0.092
Data-to-parameter ratio = 20.1
Details

5-Chloro-4'-ethyl-3H-spiro[1,3-benzothiazole-2,1'-cyclohexane]

Mehmet Akkurt,^a ^* Gökçe Cihan-Üstündag,^b Gültaze Çapan,^b Sevim Türktekin-Çelikesir ^a and Muhammad Nawaz Tahir ^c

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey, and ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C₁₄H₁₈ClNS, the 2,3-dihydro-1,3-thiazole ring adopts an envelope with the S,N-bound C atom at the flap and the cyclohexane ring adopts a chair conformation. In the crystal, N-HS hydrogen bonds with C(5) motifs connect the molecules into chains parallel to the c axis.

Related literature

For the pharmacological activity of benzothiazole derivatives, see: Coudert et al. (1988); Karali et al. (2010); Palmer et al. (1971). For standard bond lengths, see: Allen et al. (1987). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995). For ring-puckering analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₄H₁₈ClNS
M_r = 267.81
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.989 (3) Å
b = 11.163 (4) Å
c = 13.722 (4) Å
V = 1376.9 (8) Å³
Z = 4
Mo K radiation
= 0.41 mm^-1
T = 296 K
0.35 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.872, T_max = 0.903
7077 measured reflections
3203 independent reflections
2724 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.092
S = 1.03
3203 reflections
159 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.35 e Å^-3
Absolute structure: Flack (1983), 1320 Freidel pairs
Flack parameter: 0.02 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NS1ⁱ	0.84 (2)	2.84 (2)	3.669 (2)	168 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5210 ).

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Coudert, P., Couquelet, J., Sudre, O. & Bastide, J. (1988). J. Pharm. Belg. 43, 258-262.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Karali, N., Güzel, Ö., Özsoy, N., Özbey, S. & Salman, A. (2010). Eur. J. Med. Chem. 45, 1068-1077.
Palmer, P. J., Trigg, R. B. & Warrington, J. V. (1971). J. Med. Chem. 14, 248-251.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds