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

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o852

doi:10.1107/S1600536810009323

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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

(Received 8 March 2010; accepted 11 March 2010; online 17 March 2010)

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—H⋯N 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
α = 78.984 (7)°
β = 81.867 (10)°
γ = 81.718 (11)°
V = 1054.8 (4) Å³
Z = 2
Cu Kα radiation
μ = 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 > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(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
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯N2ⁱ	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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009323/hb5356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009323/hb5356Isup2.hkl

checkCIF report

Comment top

Spiro-compounds represent an important class of naturally occurring substances, which in many cases exhibit important biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are widely used for the construction of spiro-compounds (Caramella,1984). In this paper, the structure of the title compound is reported. The molecular structure of (I) is shown in Fig. 1. There exists a di-spiro ring system in the molecule which was consist of a 2-oxindole ring, a hexahydro-1H-pyrrolizine ring and a tetrahydroimidazo[2,1-b]thiazole ring. 2-oxindole ring (C8/C11/C12/C13/C14/C15/C10/N3/C9) is nearly planar that the mean deviation from this plane is 0.017Å. Two molecules are connected into a dimer by two N—H···N hydrogen bonds (Fig. 2).

Related literature top

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 top

A solution of 2-(2-chlorobenzylidene)-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one (1 mmol), isatin (1 mmol) and proline (1 mmol) in methanol (30 ml) was refluxed overnight. Completion of the reaction was evidenced by TLC analysis. The solvent was removed in vacuo. The crude product was subjected to column chromatography using petroleum ether-ethyl acetate (v/v 5:1) as eluent to afford the title compound (I). m.p.463 K; ^1Ĥ-NMR (δ, p.p.m.): 1.80-1.84 (m, 3H), 2.13-2.20 (m, 2H), 2.77-2.80 (m, 1H), 3.44-3.47 (m, 1H), 3.55-3.57 (m, 1H), 3.90-3.92 (m, 2H), 3.98-4.00 (m, 1H), 4.64-4.66 (m, 1H), 6.83 (d, J = 7.5 Hz, 1H), 7.03-7.04 (m, 1H), 7.23-7.29 (m, 2H), 7.36-7.39 (m, 2H), 7.61-7.63 (m, 1H), 7.87-7.89 (m, 1H), 8.53 (bs, 1H); 20 mg of (I) was dissolved in 15 ml dioxane-ethyl acetate mixed solvent ; the solution was kept at room temperature for 15 d by natural evaporation to give colorless blocks of (I).

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalClear (Rigaku, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
	Fig. 2. The hydrogen bonds of structure(I).

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 top

Crystal data top

C₂₄H₂₁ClN₄O₂S	Z = 2
M_r = 464.96	F(000) = 484
Triclinic, P1	D_x = 1.464 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54187 Å
a = 8.6798 (18) Å	Cell parameters from 2350 reflections
b = 11.078 (2) Å	θ = 21.5–67.5°
c = 11.372 (2) Å	µ = 2.78 mm⁻¹
α = 78.984 (7)°	T = 113 K
β = 81.867 (10)°	Block, colorless
γ = 81.718 (11)°	0.28 × 0.24 × 0.20 mm
V = 1054.8 (4) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3986 independent reflections
Radiation source: fine-focus sealed tube	3512 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.075
Detector resolution: 7.31 pixels mm^-1	θ_max = 72.1°, θ_min = 4.0°
ω and ϕ scans	h = −9→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001)	k = −13→13
T_min = 0.510, T_max = 0.606	l = −14→14
21105 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0802P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3986 reflections	Δρ_max = 0.41 e Å⁻³
294 parameters	Δρ_min = −0.53 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0128 (10)

Crystal data top

C₂₄H₂₁ClN₄O₂S	γ = 81.718 (11)°
M_r = 464.96	V = 1054.8 (4) Å³
Triclinic, P1	Z = 2
a = 8.6798 (18) Å	Cu Kα radiation
b = 11.078 (2) Å	µ = 2.78 mm⁻¹
c = 11.372 (2) Å	T = 113 K
α = 78.984 (7)°	0.28 × 0.24 × 0.20 mm
β = 81.867 (10)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.41 e Å⁻³
3986 reflections	Δρ_min = −0.53 e Å⁻³
294 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.24861 (7)	0.40648 (4)	0.48838 (4)	0.03409 (17)
S1	0.43258 (5)	0.19148 (3)	0.16037 (3)	0.01711 (15)
O1	0.13769 (14)	0.10571 (11)	0.44297 (10)	0.0206 (3)
O2	0.21446 (14)	0.28209 (11)	−0.03632 (10)	0.0211 (3)
N1	0.37173 (17)	0.02732 (13)	0.35068 (12)	0.0179 (3)
N2	0.60368 (17)	−0.02950 (13)	0.24368 (12)	0.0202 (3)
N3	0.20977 (17)	0.07131 (13)	−0.01187 (12)	0.0182 (3)
N4	−0.03261 (16)	0.24825 (12)	0.17028 (12)	0.0174 (3)
C1	0.22952 (19)	0.20199 (14)	0.23784 (13)	0.0150 (3)
C2	0.2381 (2)	0.10826 (15)	0.35725 (13)	0.0162 (3)
C3	0.4828 (2)	0.05014 (15)	0.25168 (13)	0.0165 (3)
C4	0.4173 (2)	−0.09606 (15)	0.41941 (15)	0.0219 (4)
H4A	0.3472	−0.1565	0.4119	0.026*
H4B	0.4192	−0.0936	0.5058	0.026*
C5	0.5847 (2)	−0.12500 (16)	0.35418 (15)	0.0228 (4)
H5A	0.6644	−0.1226	0.4076	0.027*
H5B	0.5979	−0.2086	0.3324	0.027*
C6	0.15375 (19)	0.33307 (14)	0.26047 (14)	0.0163 (3)
H6	0.1057	0.3231	0.3465	0.020*
C7	0.0155 (2)	0.36758 (15)	0.18111 (14)	0.0179 (3)
H7	0.0509	0.4145	0.0999	0.021*
C8	0.11006 (19)	0.16210 (15)	0.15955 (13)	0.0150 (3)
C9	0.18421 (19)	0.18303 (15)	0.02409 (14)	0.0169 (3)
C10	0.15500 (19)	−0.02286 (15)	0.07815 (14)	0.0165 (3)
C11	0.09088 (19)	0.02528 (15)	0.18252 (14)	0.0160 (3)
C12	0.0259 (2)	−0.05294 (15)	0.28191 (14)	0.0190 (4)
H12	−0.0177	−0.0220	0.3533	0.023*
C13	0.0256 (2)	−0.17737 (16)	0.27560 (16)	0.0217 (4)
H13	−0.0187	−0.2314	0.3431	0.026*
C14	0.0894 (2)	−0.22283 (16)	0.17121 (16)	0.0228 (4)
H14	0.0880	−0.3078	0.1684	0.027*
C15	0.1554 (2)	−0.14631 (15)	0.07089 (15)	0.0214 (4)
H15	0.1992	−0.1777	−0.0003	0.026*
C16	−0.1309 (2)	0.43859 (16)	0.24054 (16)	0.0237 (4)
H16A	−0.1688	0.5132	0.1843	0.028*
H16B	−0.1082	0.4641	0.3145	0.028*
C17	−0.2531 (2)	0.34589 (17)	0.27121 (18)	0.0287 (4)
H17A	−0.3134	0.3511	0.3511	0.034*
H17B	−0.3268	0.3617	0.2095	0.034*
C18	−0.1555 (2)	0.21991 (16)	0.27193 (16)	0.0220 (4)
H18A	−0.1101	0.1902	0.3489	0.026*
H18B	−0.2182	0.1573	0.2577	0.026*
C19	0.2614 (2)	0.43184 (15)	0.24310 (14)	0.0179 (3)
C20	0.3102 (2)	0.47270 (15)	0.33957 (15)	0.0208 (4)
C21	0.4077 (2)	0.56475 (16)	0.32325 (17)	0.0261 (4)
H21	0.4377	0.5904	0.3909	0.031*
C22	0.4612 (2)	0.61903 (16)	0.20712 (18)	0.0266 (4)
H22	0.5288	0.6817	0.1945	0.032*
C23	0.4147 (2)	0.58077 (16)	0.10959 (16)	0.0253 (4)
H23	0.4500	0.6179	0.0298	0.030*
C24	0.3173 (2)	0.48903 (16)	0.12801 (15)	0.0222 (4)
H24	0.2874	0.4641	0.0599	0.027*
H1	0.255 (3)	0.064 (2)	−0.085 (2)	0.032 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0545 (4)	0.0322 (3)	0.0213 (2)	−0.0151 (2)	−0.0128 (2)	−0.00515 (18)
S1	0.0177 (2)	0.0147 (2)	0.0184 (2)	0.00019 (16)	−0.00128 (15)	−0.00395 (15)
O1	0.0237 (7)	0.0229 (6)	0.0163 (6)	−0.0034 (5)	−0.0004 (5)	−0.0073 (4)
O2	0.0280 (7)	0.0175 (6)	0.0183 (6)	−0.0026 (5)	−0.0036 (5)	−0.0037 (4)
N1	0.0221 (8)	0.0151 (7)	0.0167 (6)	0.0001 (6)	−0.0035 (5)	−0.0039 (5)
N2	0.0233 (8)	0.0173 (7)	0.0213 (7)	0.0020 (6)	−0.0052 (6)	−0.0083 (5)
N3	0.0240 (8)	0.0164 (7)	0.0156 (7)	0.0008 (6)	−0.0024 (5)	−0.0089 (5)
N4	0.0185 (7)	0.0142 (7)	0.0213 (7)	0.0019 (6)	−0.0037 (5)	−0.0096 (5)
C1	0.0170 (8)	0.0151 (8)	0.0142 (7)	−0.0015 (6)	−0.0004 (6)	−0.0073 (6)
C2	0.0214 (9)	0.0145 (8)	0.0156 (7)	−0.0035 (6)	−0.0042 (6)	−0.0070 (6)
C3	0.0202 (9)	0.0148 (8)	0.0172 (7)	−0.0017 (7)	−0.0049 (6)	−0.0079 (6)
C4	0.0292 (10)	0.0141 (8)	0.0223 (8)	0.0004 (7)	−0.0072 (7)	−0.0024 (6)
C5	0.0290 (10)	0.0166 (8)	0.0237 (8)	0.0030 (7)	−0.0080 (7)	−0.0065 (6)
C6	0.0190 (9)	0.0141 (8)	0.0176 (7)	−0.0007 (6)	−0.0021 (6)	−0.0082 (6)
C7	0.0209 (9)	0.0124 (8)	0.0219 (8)	0.0007 (7)	−0.0045 (6)	−0.0076 (6)
C8	0.0171 (8)	0.0154 (8)	0.0144 (7)	−0.0006 (6)	−0.0024 (6)	−0.0078 (5)
C9	0.0184 (8)	0.0176 (8)	0.0162 (7)	0.0018 (6)	−0.0055 (6)	−0.0075 (6)
C10	0.0159 (8)	0.0174 (8)	0.0181 (7)	0.0017 (6)	−0.0050 (6)	−0.0081 (6)
C11	0.0166 (8)	0.0148 (8)	0.0190 (7)	0.0010 (6)	−0.0050 (6)	−0.0089 (6)
C12	0.0204 (9)	0.0185 (8)	0.0200 (8)	−0.0012 (7)	−0.0036 (6)	−0.0080 (6)
C13	0.0205 (9)	0.0179 (8)	0.0270 (8)	−0.0030 (7)	−0.0037 (7)	−0.0033 (6)
C14	0.0240 (10)	0.0138 (8)	0.0335 (9)	0.0013 (7)	−0.0082 (7)	−0.0101 (7)
C15	0.0253 (9)	0.0178 (8)	0.0238 (8)	0.0037 (7)	−0.0063 (7)	−0.0126 (6)
C16	0.0228 (9)	0.0187 (9)	0.0319 (9)	0.0035 (7)	−0.0052 (7)	−0.0130 (7)
C17	0.0216 (10)	0.0236 (10)	0.0416 (10)	0.0026 (8)	−0.0005 (8)	−0.0139 (8)
C18	0.0189 (9)	0.0194 (8)	0.0289 (9)	−0.0003 (7)	−0.0008 (7)	−0.0101 (6)
C19	0.0200 (9)	0.0116 (7)	0.0238 (8)	0.0028 (6)	−0.0037 (6)	−0.0101 (6)
C20	0.0238 (9)	0.0159 (8)	0.0251 (8)	0.0012 (7)	−0.0077 (7)	−0.0082 (6)
C21	0.0259 (10)	0.0185 (9)	0.0381 (10)	0.0006 (7)	−0.0108 (8)	−0.0127 (7)
C22	0.0226 (10)	0.0163 (9)	0.0438 (11)	−0.0034 (7)	−0.0020 (8)	−0.0132 (7)
C23	0.0277 (10)	0.0172 (8)	0.0302 (9)	−0.0021 (7)	0.0045 (7)	−0.0083 (7)
C24	0.0271 (10)	0.0167 (8)	0.0242 (8)	0.0009 (7)	−0.0016 (7)	−0.0106 (6)

Geometric parameters (Å, º) top

Cl1—C20	1.7522 (18)	C8—C9	1.571 (2)
S1—C3	1.7407 (16)	C10—C15	1.385 (2)
S1—C1	1.8539 (17)	C10—C11	1.404 (2)
O1—C2	1.211 (2)	C11—C12	1.390 (2)
O2—C9	1.220 (2)	C12—C13	1.394 (2)
N1—C2	1.363 (2)	C12—H12	0.9500
N1—C3	1.384 (2)	C13—C14	1.390 (2)
N1—C4	1.469 (2)	C13—H13	0.9500
N2—C3	1.275 (2)	C14—C15	1.390 (3)
N2—C5	1.486 (2)	C14—H14	0.9500
N3—C9	1.355 (2)	C15—H15	0.9500
N3—C10	1.400 (2)	C16—C17	1.540 (3)
N3—H1	0.88 (2)	C16—H16A	0.9900
N4—C8	1.456 (2)	C16—H16B	0.9900
N4—C7	1.474 (2)	C17—C18	1.524 (2)
N4—C18	1.477 (2)	C17—H17A	0.9900
C1—C2	1.548 (2)	C17—H17B	0.9900
C1—C6	1.558 (2)	C18—H18A	0.9900
C1—C8	1.614 (2)	C18—H18B	0.9900
C4—C5	1.555 (3)	C19—C24	1.394 (2)
C4—H4A	0.9900	C19—C20	1.401 (2)
C4—H4B	0.9900	C20—C21	1.387 (3)
C5—H5A	0.9900	C21—C22	1.387 (3)
C5—H5B	0.9900	C21—H21	0.9500
C6—C19	1.507 (2)	C22—C23	1.389 (3)
C6—C7	1.563 (2)	C22—H22	0.9500
C6—H6	1.0000	C23—C24	1.381 (3)
C7—C16	1.537 (2)	C23—H23	0.9500
C7—H7	1.0000	C24—H24	0.9500
C8—C11	1.517 (2)

C3—S1—C1	91.34 (8)	N3—C9—C8	107.47 (13)
C2—N1—C3	118.08 (13)	C15—C10—N3	127.81 (15)
C2—N1—C4	132.63 (14)	C15—C10—C11	121.99 (16)
C3—N1—C4	108.49 (13)	N3—C10—C11	110.17 (14)
C3—N2—C5	105.37 (14)	C12—C11—C10	119.27 (15)
C9—N3—C10	112.22 (13)	C12—C11—C8	132.62 (14)
C9—N3—H1	120.9 (15)	C10—C11—C8	108.11 (14)
C10—N3—H1	126.9 (15)	C11—C12—C13	119.24 (15)
C8—N4—C7	106.79 (13)	C11—C12—H12	120.4
C8—N4—C18	119.35 (13)	C13—C12—H12	120.4
C7—N4—C18	106.15 (12)	C14—C13—C12	120.45 (17)
C2—C1—C6	111.70 (12)	C14—C13—H13	119.8
C2—C1—C8	109.24 (13)	C12—C13—H13	119.8
C6—C1—C8	103.51 (12)	C13—C14—C15	121.26 (16)
C2—C1—S1	104.85 (11)	C13—C14—H14	119.4
C6—C1—S1	116.29 (11)	C15—C14—H14	119.4
C8—C1—S1	111.25 (10)	C10—C15—C14	117.79 (15)
O1—C2—N1	125.06 (15)	C10—C15—H15	121.1
O1—C2—C1	124.45 (15)	C14—C15—H15	121.1
N1—C2—C1	110.46 (13)	C7—C16—C17	104.65 (13)
N2—C3—N1	117.43 (14)	C7—C16—H16A	110.8
N2—C3—S1	130.89 (13)	C17—C16—H16A	110.8
N1—C3—S1	111.62 (12)	C7—C16—H16B	110.8
N1—C4—C5	99.92 (13)	C17—C16—H16B	110.8
N1—C4—H4A	111.8	H16A—C16—H16B	108.9
C5—C4—H4A	111.8	C18—C17—C16	104.10 (15)
N1—C4—H4B	111.8	C18—C17—H17A	110.9
C5—C4—H4B	111.8	C16—C17—H17A	110.9
H4A—C4—H4B	109.5	C18—C17—H17B	110.9
N2—C5—C4	107.58 (13)	C16—C17—H17B	110.9
N2—C5—H5A	110.2	H17A—C17—H17B	109.0
C4—C5—H5A	110.2	N4—C18—C17	101.57 (14)
N2—C5—H5B	110.2	N4—C18—H18A	111.5
C4—C5—H5B	110.2	C17—C18—H18A	111.5
H5A—C5—H5B	108.5	N4—C18—H18B	111.5
C19—C6—C1	117.03 (14)	C17—C18—H18B	111.5
C19—C6—C7	113.84 (13)	H18A—C18—H18B	109.3
C1—C6—C7	105.08 (12)	C24—C19—C20	116.04 (16)
C19—C6—H6	106.8	C24—C19—C6	121.04 (15)
C1—C6—H6	106.8	C20—C19—C6	122.91 (15)
C7—C6—H6	106.8	C21—C20—C19	122.76 (17)
N4—C7—C16	105.48 (14)	C21—C20—Cl1	117.18 (13)
N4—C7—C6	105.24 (12)	C19—C20—Cl1	120.06 (14)
C16—C7—C6	113.85 (13)	C20—C21—C22	119.36 (17)
N4—C7—H7	110.7	C20—C21—H21	120.3
C16—C7—H7	110.7	C22—C21—H21	120.3
C6—C7—H7	110.7	C21—C22—C23	119.26 (18)
N4—C8—C11	116.83 (14)	C21—C22—H22	120.4
N4—C8—C9	108.11 (12)	C23—C22—H22	120.4
C11—C8—C9	101.84 (12)	C24—C23—C22	120.37 (17)
N4—C8—C1	106.18 (12)	C24—C23—H23	119.8
C11—C8—C1	115.78 (12)	C22—C23—H23	119.8
C9—C8—C1	107.48 (13)	C23—C24—C19	122.21 (16)
O2—C9—N3	126.81 (15)	C23—C24—H24	118.9
O2—C9—C8	125.72 (14)	C19—C24—H24	118.9

C3—S1—C1—C2	17.34 (11)	C2—C1—C8—C9	−139.50 (13)
C3—S1—C1—C6	141.23 (11)	C6—C1—C8—C9	101.38 (13)
C3—S1—C1—C8	−100.62 (11)	S1—C1—C8—C9	−24.22 (14)
C3—N1—C2—O1	−173.38 (15)	C10—N3—C9—O2	−177.34 (16)
C4—N1—C2—O1	18.2 (3)	C10—N3—C9—C8	3.48 (18)
C3—N1—C2—C1	8.4 (2)	N4—C8—C9—O2	52.9 (2)
C4—N1—C2—C1	−159.95 (16)	C11—C8—C9—O2	176.57 (16)
C6—C1—C2—O1	37.6 (2)	C1—C8—C9—O2	−61.3 (2)
C8—C1—C2—O1	−76.26 (19)	N4—C8—C9—N3	−127.87 (14)
S1—C1—C2—O1	164.42 (14)	C11—C8—C9—N3	−4.24 (16)
C6—C1—C2—N1	−144.15 (14)	C1—C8—C9—N3	117.90 (14)
C8—C1—C2—N1	101.94 (15)	C9—N3—C10—C15	176.92 (16)
S1—C1—C2—N1	−17.38 (15)	C9—N3—C10—C11	−1.15 (19)
C5—N2—C3—N1	−1.89 (19)	C15—C10—C11—C12	0.1 (2)
C5—N2—C3—S1	175.10 (13)	N3—C10—C11—C12	178.33 (14)
C2—N1—C3—N2	−176.64 (14)	C15—C10—C11—C8	179.98 (14)
C4—N1—C3—N2	−5.6 (2)	N3—C10—C11—C8	−1.82 (18)
C2—N1—C3—S1	5.81 (19)	N4—C8—C11—C12	−59.1 (2)
C4—N1—C3—S1	176.82 (11)	C9—C8—C11—C12	−176.61 (17)
C1—S1—C3—N2	168.82 (16)	C1—C8—C11—C12	67.1 (2)
C1—S1—C3—N1	−14.05 (12)	N4—C8—C11—C10	121.09 (14)
C2—N1—C4—C5	178.86 (16)	C9—C8—C11—C10	3.57 (16)
C3—N1—C4—C5	9.66 (16)	C1—C8—C11—C10	−112.67 (15)
C3—N2—C5—C4	8.22 (18)	C10—C11—C12—C13	−0.2 (2)
N1—C4—C5—N2	−10.75 (16)	C8—C11—C12—C13	−179.98 (16)
C2—C1—C6—C19	107.20 (16)	C11—C12—C13—C14	0.0 (3)
C8—C1—C6—C19	−135.39 (13)	C12—C13—C14—C15	0.1 (3)
S1—C1—C6—C19	−13.08 (17)	N3—C10—C15—C14	−177.82 (16)
C2—C1—C6—C7	−125.40 (14)	C11—C10—C15—C14	0.0 (2)
C8—C1—C6—C7	−7.99 (15)	C13—C14—C15—C10	−0.2 (3)
S1—C1—C6—C7	114.32 (12)	N4—C7—C16—C17	5.22 (17)
C8—N4—C7—C16	−158.43 (12)	C6—C7—C16—C17	−109.65 (16)
C18—N4—C7—C16	−30.09 (16)	C7—C16—C17—C18	20.32 (18)
C8—N4—C7—C6	−37.75 (15)	C8—N4—C18—C17	163.22 (14)
C18—N4—C7—C6	90.59 (14)	C7—N4—C18—C17	42.69 (16)
C19—C6—C7—N4	156.75 (13)	C16—C17—C18—N4	−38.17 (17)
C1—C6—C7—N4	27.44 (16)	C1—C6—C19—C24	76.18 (19)
C19—C6—C7—C16	−88.23 (17)	C7—C6—C19—C24	−46.8 (2)
C1—C6—C7—C16	142.45 (14)	C1—C6—C19—C20	−104.47 (18)
C7—N4—C8—C11	163.22 (13)	C7—C6—C19—C20	132.52 (16)
C18—N4—C8—C11	43.02 (19)	C24—C19—C20—C21	0.2 (2)
C7—N4—C8—C9	−82.74 (14)	C6—C19—C20—C21	−179.17 (15)
C18—N4—C8—C9	157.06 (14)	C24—C19—C20—Cl1	−179.45 (12)
C7—N4—C8—C1	32.35 (15)	C6—C19—C20—Cl1	1.2 (2)
C18—N4—C8—C1	−87.84 (16)	C19—C20—C21—C22	−0.4 (3)
C2—C1—C8—N4	104.98 (14)	Cl1—C20—C21—C22	179.24 (13)
C6—C1—C8—N4	−14.14 (15)	C20—C21—C22—C23	0.6 (3)
S1—C1—C8—N4	−139.74 (11)	C21—C22—C23—C24	−0.5 (3)
C2—C1—C8—C11	−26.48 (18)	C22—C23—C24—C19	0.3 (3)
C6—C1—C8—C11	−145.59 (13)	C20—C19—C24—C23	−0.1 (2)
S1—C1—C8—C11	88.80 (14)	C6—C19—C24—C23	179.24 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···N2ⁱ	0.88 (2)	2.10 (2)	2.971 (2)	170 (2)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁ClN₄O₂S
M_r	464.96
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	8.6798 (18), 11.078 (2), 11.372 (2)
α, β, γ (°)	78.984 (7), 81.867 (10), 81.718 (11)
V (Å³)	1054.8 (4)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.78
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2001)
T_min, T_max	0.510, 0.606
No. of measured, independent and observed [I > 2σ(I)] reflections	21105, 3986, 3512
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 1.02
No. of reflections	3986
No. of parameters	294
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.53

Computer programs: CrystalClear (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···N2ⁱ	0.88 (2)	2.10 (2)	2.971 (2)	170 (2)

Symmetry code: (i) −x+1, −y, −z.

References

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

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Volume 66| Part 4| April 2010| Page o852

doi:10.1107/S1600536810009323

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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