N-(3-Oxo-1-thia-4-aza­spiro­[4.5]dec-4-yl)-6-phenyl­imidazo[2,1-b][1,3]thia­zole-3-acetamide hemihydrate

Akkurt, M.; Yalçın, Ş.P.; Güzeldemirci, N.U.; Büyükgüngör, O.

doi:10.1107/S1600536808009306

Volume 64
Part 5
Pages o810-o811
May 2008

Received 3 April 2008
Accepted 6 April 2008
Online 10 April 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.098
Data-to-parameter ratio = 15.5
Details

N-(3-Oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-6-phenylimidazo[2,1-b][1,3]thiazole-3-acetamide hemihydrate

Mehmet Akkurt,^a ^* Serife Pinar Yalçin,^a Nuray Ulusoy Güzeldemirci ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey,^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Istanbul, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

The title compound, C₂₁H₂₂N₄O₂S₂·0.5H₂O, crystallizes with two molecules in the asymmetric unit. The dihedral angles between the phenyl and imidazothiazole ring systems are 19.16 (9) and 21.37 (9)°. In the imidazothiazole ring systems, the cyclohexane rings adopt chair conformations, while the thiazole rings have distorted envelope conformations. The two molecules are stabilized by intramolecular N-HO, O-HO and C-HS interactions and the crystal structure is stabilized by intermolecular N-HO, O-HO, C-HO and C-HN interactions.

Related literature

For related literature, see: Akkurt et al. (2005, 2007); Allen et al. (1987); Amarouch et al. (1988); Andreani et al. (1998); Cremer & Pople (1975); Devlin & Hargrave (1989); Gürsoy & Ulusoy Güzeldemirci (2007); Srimanth et al. (2002); Ulusoy (2002); Ur et al. (2004); Öztürk Yildirim, Akkurt, Ur, Cesur, Cesur & Büyükgüngör (2005); Öztürk Yildirim, Akkurt, Ur, Cesur, Cesur & Heinemann (2005).

Experimental

Crystal data

C₂₁H₂₂N₄O₂S₂·0.5H₂O
M_r = 435.58
Triclinic, $[P \overline 1]$
a = 11.0175 (3) Å
b = 11.8817 (3) Å
c = 17.6162 (5) Å
= 75.123 (2)°
= 73.502 (2)°
= 81.012 (2)°
V = 2128.36 (10) Å³
Z = 4
Mo K radiation
= 0.28 mm^-1
T = 296 K
0.52 × 0.39 × 0.25 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.869, T_max = 0.934
38012 measured reflections
8351 independent reflections
6705 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.098
S = 1.02
8351 reflections
538 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO3	0.86	1.98	2.841 (2)	175
O5-H5AO1	0.833 (19)	1.880 (19)	2.7097 (19)	174.4 (18)
O5-H5BO4ⁱ	0.848 (18)	1.917 (18)	2.764 (2)	177 (2)
N7-H7O5ⁱⁱ	0.86	1.94	2.7617 (19)	160
C10-H10O4ⁱ	0.93	2.41	3.306 (2)	161
C12-H12AO2ⁱ	0.97	2.48	3.074 (2)	120
C15-H15BN2ⁱⁱⁱ	0.97	2.57	3.462 (3)	153
C18-H18AS2	0.97	2.87	3.255 (2)	105
C20-H20BS2	0.97	2.84	3.227 (3)	105
C21-H21AS4	0.97	2.83	3.768 (2)	163
C33-H33BO5ⁱⁱ	0.97	2.54	3.376 (2)	144
C36-H36BN6ⁱⁱⁱ	0.97	2.56	3.448 (3)	153
C39-H39AS4	0.97	2.87	3.246 (2)	104
C41-H41BS4	0.97	2.78	3.194 (2)	106
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x, y+1, z; (iii) x+1, y, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2390 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

References

Akkurt, M., Yalçin, S. P., Gürsoy, E., Güzeldemirci, N. U. & Büyükgüngör, O. (2007). Acta Cryst. E63, o3103.
Akkurt, M., Yildirim, S. Ö., Ur, F., Cesur, Z., Cesur, N. & Büyükgüngör, O. (2005). Acta Cryst. E61, o718-o720.
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.
Amarouch, H., Loiseau, P. R., Bonnafous, M., Caujolle, R., Payard, M., Loiseau, P. M., Bories, C. & Gayral, P. (1988). Farmaco Ed. Sci. 43, 421-437.
Andreani, A., Leoni, A., Morigi, R., Bossa, R., Chiericozzi, M. & Galatulas, I. (1998). Arzneim. Forsch. Drug. Res. 48, 232-235.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Devlin, J. P. & Hargrave, K. D. (1989). Tetrahedron, 45, 4327-4369.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gürsoy, E. & Ulusoy Güzeldemirci, N. (2007). Eur. J. Med. Chem. 42, 320-326.
Öztürk Yildirim, S., Akkurt, M., Ur, F., Cesur, Z., Cesur, N. & Büyükgüngör, O. (2005). Acta Cryst. E61, o892-o894.
Öztürk Yildirim, S., Akkurt, M., Ur, F., Cesur, Z., Cesur, N. & Heinemann, F. W. (2005). Acta Cryst. E61, o2357-o2359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Srimanth, K., Rao, V. R. & Krishna, D. R. (2002). Arzneim. Forsch. Drug. Res. 52, 388-392.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Ulusoy, N. (2002). Arzneim. Forsch. Drug. Res. 52, 565-571.
Ur, F., Cesur, N., Birteksöz, S. & Ötük, G. (2004). Arzneim. Forsch. Drug. Res. 54, 125-129.

organic compounds