1′-(2-Chloro­phen­yl)-5,6,5′,6′,7′,7a′-hexa­hydro-1′H,1′′H-dispiro­[imidazo[2,1-b][1,3]thia­zole-2,2′-pyrrolizine-3′(2′H),3′′-indole]-2′′,3(2H,3′′H)-dione

Liao, B.; Zheng, A.; Liu, B.

doi:10.1107/S1600536810009323

Volume 66
Part 4
Page o852
April 2010

Received 8 March 2010
Accepted 11 March 2010
Online 17 March 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.113
Data-to-parameter ratio = 13.6
Details

1'-(2-Chlorophenyl)-5,6,5',6',7',7a'-hexahydro-1'H,1''H-dispiro[imidazo[2,1-b][1,3]thiazole-2,2'-pyrrolizine-3'(2'H),3''-indole]-2'',3(2H,3''H)-dione

Bo Liao,^a ^* Aiting Zheng ^a and Bin Liu ^a

^aSchool of of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, People's Republic of China
Correspondence e-mail: liaobohnust@163.com

In the title compound, C₂₄H₂₁ClN₄O₂S, the two adjacent spiro junctions link an almost planar (r.m.s. deviation = 0.017 Å) 2-oxindole ring, a hexahydro-1H-pyrrolizine ring and a tetrahydroimidazo[2,1-b]thiazole ring. In the crystal, inversion dimers linked by pairs of N-HN hydrogen bonds occur, generating an R₂²(16) loop.

Related literature

For backgound to the properties of spiro-compounds, see: James et al. (1991); Kobayashi et al. (1991). For further synthetic details, see: Caramella & Grunanger (1984).

Experimental

Crystal data

C₂₄H₂₁ClN₄O₂S
M_r = 464.96
Triclinic, $[P \overline 1]$
a = 8.6798 (18) Å
b = 11.078 (2) Å
c = 11.372 (2) Å
= 78.984 (7)°
= 81.867 (10)°
= 81.718 (11)°
V = 1054.8 (4) Å³
Z = 2
Cu K radiation
= 2.78 mm^-1
T = 113 K
0.28 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001) T_min = 0.510, T_max = 0.606
21105 measured reflections
3986 independent reflections
3512 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.113
S = 1.02
3986 reflections
294 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.41 e Å^-3
_min = -0.53 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1N2ⁱ	0.88 (2)	2.10 (2)	2.971 (2)	170 (2)
Symmetry code: (i) -x+1, -y, -z.

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5356 ).

References

Caramella, P. & Grunanger, P. (1984). 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, edited by A. Padwa, pp. 291-312. New York: Wiley.
James, D., Kunze, H. B. & Faulkner, D. (1991). J. Nat. Prod. 54, 1137-1140.
Kobayashi, J., Tsuda, M., Agemi, K. & Vacelet, J. (1991). Tetrahedron, 47, 6617-6622.
Rigaku (2001). CrystalClear . Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds