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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o852.
Published online 2010 March 17. doi:  10.1107/S1600536810009323
PMCID: PMC2983913

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

Abstract

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 R 2 2(16) loop.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-66-0o852-scheme1.jpg

Experimental

Crystal data

  • C24H21ClN4O2S
  • M r = 464.96
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o852-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.113
  • S = 1.02
  • 3986 reflections
  • 294 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.53 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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).

Experimental

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).

Figures

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

Crystal data

C24H21ClN4O2SZ = 2
Mr = 464.96F(000) = 484
Triclinic, P1Dx = 1.464 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54187 Å
a = 8.6798 (18) ÅCell parameters from 2350 reflections
b = 11.078 (2) Åθ = 21.5–67.5°
c = 11.372 (2) ŵ = 2.78 mm1
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

Rigaku Saturn CCD area-detector diffractometer3986 independent reflections
Radiation source: fine-focus sealed tube3512 reflections with I > 2σ(I)
multilayerRint = 0.075
Detector resolution: 7.31 pixels mm-1θmax = 72.1°, θmin = 4.0°
ω and [var phi] scansh = −9→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2001)k = −13→13
Tmin = 0.510, Tmax = 0.606l = −14→14
21105 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113w = 1/[σ2(Fo2) + (0.0802P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3986 reflectionsΔρmax = 0.41 e Å3
294 parametersΔρmin = −0.53 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0128 (10)

Special details

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)

xyzUiso*/Ueq
Cl10.24861 (7)0.40648 (4)0.48838 (4)0.03409 (17)
S10.43258 (5)0.19148 (3)0.16037 (3)0.01711 (15)
O10.13769 (14)0.10571 (11)0.44297 (10)0.0206 (3)
O20.21446 (14)0.28209 (11)−0.03632 (10)0.0211 (3)
N10.37173 (17)0.02732 (13)0.35068 (12)0.0179 (3)
N20.60368 (17)−0.02950 (13)0.24368 (12)0.0202 (3)
N30.20977 (17)0.07131 (13)−0.01187 (12)0.0182 (3)
N4−0.03261 (16)0.24825 (12)0.17028 (12)0.0174 (3)
C10.22952 (19)0.20199 (14)0.23784 (13)0.0150 (3)
C20.2381 (2)0.10826 (15)0.35725 (13)0.0162 (3)
C30.4828 (2)0.05014 (15)0.25168 (13)0.0165 (3)
C40.4173 (2)−0.09606 (15)0.41941 (15)0.0219 (4)
H4A0.3472−0.15650.41190.026*
H4B0.4192−0.09360.50580.026*
C50.5847 (2)−0.12500 (16)0.35418 (15)0.0228 (4)
H5A0.6644−0.12260.40760.027*
H5B0.5979−0.20860.33240.027*
C60.15375 (19)0.33307 (14)0.26047 (14)0.0163 (3)
H60.10570.32310.34650.020*
C70.0155 (2)0.36758 (15)0.18111 (14)0.0179 (3)
H70.05090.41450.09990.021*
C80.11006 (19)0.16210 (15)0.15955 (13)0.0150 (3)
C90.18421 (19)0.18303 (15)0.02409 (14)0.0169 (3)
C100.15500 (19)−0.02286 (15)0.07815 (14)0.0165 (3)
C110.09088 (19)0.02528 (15)0.18252 (14)0.0160 (3)
C120.0259 (2)−0.05294 (15)0.28191 (14)0.0190 (4)
H12−0.0177−0.02200.35330.023*
C130.0256 (2)−0.17737 (16)0.27560 (16)0.0217 (4)
H13−0.0187−0.23140.34310.026*
C140.0894 (2)−0.22283 (16)0.17121 (16)0.0228 (4)
H140.0880−0.30780.16840.027*
C150.1554 (2)−0.14631 (15)0.07089 (15)0.0214 (4)
H150.1992−0.1777−0.00030.026*
C16−0.1309 (2)0.43859 (16)0.24054 (16)0.0237 (4)
H16A−0.16880.51320.18430.028*
H16B−0.10820.46410.31450.028*
C17−0.2531 (2)0.34589 (17)0.27121 (18)0.0287 (4)
H17A−0.31340.35110.35110.034*
H17B−0.32680.36170.20950.034*
C18−0.1555 (2)0.21991 (16)0.27193 (16)0.0220 (4)
H18A−0.11010.19020.34890.026*
H18B−0.21820.15730.25770.026*
C190.2614 (2)0.43184 (15)0.24310 (14)0.0179 (3)
C200.3102 (2)0.47270 (15)0.33957 (15)0.0208 (4)
C210.4077 (2)0.56475 (16)0.32325 (17)0.0261 (4)
H210.43770.59040.39090.031*
C220.4612 (2)0.61903 (16)0.20712 (18)0.0266 (4)
H220.52880.68170.19450.032*
C230.4147 (2)0.58077 (16)0.10959 (16)0.0253 (4)
H230.45000.61790.02980.030*
C240.3173 (2)0.48903 (16)0.12801 (15)0.0222 (4)
H240.28740.46410.05990.027*
H10.255 (3)0.064 (2)−0.085 (2)0.032 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0545 (4)0.0322 (3)0.0213 (2)−0.0151 (2)−0.0128 (2)−0.00515 (18)
S10.0177 (2)0.0147 (2)0.0184 (2)0.00019 (16)−0.00128 (15)−0.00395 (15)
O10.0237 (7)0.0229 (6)0.0163 (6)−0.0034 (5)−0.0004 (5)−0.0073 (4)
O20.0280 (7)0.0175 (6)0.0183 (6)−0.0026 (5)−0.0036 (5)−0.0037 (4)
N10.0221 (8)0.0151 (7)0.0167 (6)0.0001 (6)−0.0035 (5)−0.0039 (5)
N20.0233 (8)0.0173 (7)0.0213 (7)0.0020 (6)−0.0052 (6)−0.0083 (5)
N30.0240 (8)0.0164 (7)0.0156 (7)0.0008 (6)−0.0024 (5)−0.0089 (5)
N40.0185 (7)0.0142 (7)0.0213 (7)0.0019 (6)−0.0037 (5)−0.0096 (5)
C10.0170 (8)0.0151 (8)0.0142 (7)−0.0015 (6)−0.0004 (6)−0.0073 (6)
C20.0214 (9)0.0145 (8)0.0156 (7)−0.0035 (6)−0.0042 (6)−0.0070 (6)
C30.0202 (9)0.0148 (8)0.0172 (7)−0.0017 (7)−0.0049 (6)−0.0079 (6)
C40.0292 (10)0.0141 (8)0.0223 (8)0.0004 (7)−0.0072 (7)−0.0024 (6)
C50.0290 (10)0.0166 (8)0.0237 (8)0.0030 (7)−0.0080 (7)−0.0065 (6)
C60.0190 (9)0.0141 (8)0.0176 (7)−0.0007 (6)−0.0021 (6)−0.0082 (6)
C70.0209 (9)0.0124 (8)0.0219 (8)0.0007 (7)−0.0045 (6)−0.0076 (6)
C80.0171 (8)0.0154 (8)0.0144 (7)−0.0006 (6)−0.0024 (6)−0.0078 (5)
C90.0184 (8)0.0176 (8)0.0162 (7)0.0018 (6)−0.0055 (6)−0.0075 (6)
C100.0159 (8)0.0174 (8)0.0181 (7)0.0017 (6)−0.0050 (6)−0.0081 (6)
C110.0166 (8)0.0148 (8)0.0190 (7)0.0010 (6)−0.0050 (6)−0.0089 (6)
C120.0204 (9)0.0185 (8)0.0200 (8)−0.0012 (7)−0.0036 (6)−0.0080 (6)
C130.0205 (9)0.0179 (8)0.0270 (8)−0.0030 (7)−0.0037 (7)−0.0033 (6)
C140.0240 (10)0.0138 (8)0.0335 (9)0.0013 (7)−0.0082 (7)−0.0101 (7)
C150.0253 (9)0.0178 (8)0.0238 (8)0.0037 (7)−0.0063 (7)−0.0126 (6)
C160.0228 (9)0.0187 (9)0.0319 (9)0.0035 (7)−0.0052 (7)−0.0130 (7)
C170.0216 (10)0.0236 (10)0.0416 (10)0.0026 (8)−0.0005 (8)−0.0139 (8)
C180.0189 (9)0.0194 (8)0.0289 (9)−0.0003 (7)−0.0008 (7)−0.0101 (6)
C190.0200 (9)0.0116 (7)0.0238 (8)0.0028 (6)−0.0037 (6)−0.0101 (6)
C200.0238 (9)0.0159 (8)0.0251 (8)0.0012 (7)−0.0077 (7)−0.0082 (6)
C210.0259 (10)0.0185 (9)0.0381 (10)0.0006 (7)−0.0108 (8)−0.0127 (7)
C220.0226 (10)0.0163 (9)0.0438 (11)−0.0034 (7)−0.0020 (8)−0.0132 (7)
C230.0277 (10)0.0172 (8)0.0302 (9)−0.0021 (7)0.0045 (7)−0.0083 (7)
C240.0271 (10)0.0167 (8)0.0242 (8)0.0009 (7)−0.0016 (7)−0.0106 (6)

Geometric parameters (Å, °)

Cl1—C201.7522 (18)C8—C91.571 (2)
S1—C31.7407 (16)C10—C151.385 (2)
S1—C11.8539 (17)C10—C111.404 (2)
O1—C21.211 (2)C11—C121.390 (2)
O2—C91.220 (2)C12—C131.394 (2)
N1—C21.363 (2)C12—H120.9500
N1—C31.384 (2)C13—C141.390 (2)
N1—C41.469 (2)C13—H130.9500
N2—C31.275 (2)C14—C151.390 (3)
N2—C51.486 (2)C14—H140.9500
N3—C91.355 (2)C15—H150.9500
N3—C101.400 (2)C16—C171.540 (3)
N3—H10.88 (2)C16—H16A0.9900
N4—C81.456 (2)C16—H16B0.9900
N4—C71.474 (2)C17—C181.524 (2)
N4—C181.477 (2)C17—H17A0.9900
C1—C21.548 (2)C17—H17B0.9900
C1—C61.558 (2)C18—H18A0.9900
C1—C81.614 (2)C18—H18B0.9900
C4—C51.555 (3)C19—C241.394 (2)
C4—H4A0.9900C19—C201.401 (2)
C4—H4B0.9900C20—C211.387 (3)
C5—H5A0.9900C21—C221.387 (3)
C5—H5B0.9900C21—H210.9500
C6—C191.507 (2)C22—C231.389 (3)
C6—C71.563 (2)C22—H220.9500
C6—H61.0000C23—C241.381 (3)
C7—C161.537 (2)C23—H230.9500
C7—H71.0000C24—H240.9500
C8—C111.517 (2)
C3—S1—C191.34 (8)N3—C9—C8107.47 (13)
C2—N1—C3118.08 (13)C15—C10—N3127.81 (15)
C2—N1—C4132.63 (14)C15—C10—C11121.99 (16)
C3—N1—C4108.49 (13)N3—C10—C11110.17 (14)
C3—N2—C5105.37 (14)C12—C11—C10119.27 (15)
C9—N3—C10112.22 (13)C12—C11—C8132.62 (14)
C9—N3—H1120.9 (15)C10—C11—C8108.11 (14)
C10—N3—H1126.9 (15)C11—C12—C13119.24 (15)
C8—N4—C7106.79 (13)C11—C12—H12120.4
C8—N4—C18119.35 (13)C13—C12—H12120.4
C7—N4—C18106.15 (12)C14—C13—C12120.45 (17)
C2—C1—C6111.70 (12)C14—C13—H13119.8
C2—C1—C8109.24 (13)C12—C13—H13119.8
C6—C1—C8103.51 (12)C13—C14—C15121.26 (16)
C2—C1—S1104.85 (11)C13—C14—H14119.4
C6—C1—S1116.29 (11)C15—C14—H14119.4
C8—C1—S1111.25 (10)C10—C15—C14117.79 (15)
O1—C2—N1125.06 (15)C10—C15—H15121.1
O1—C2—C1124.45 (15)C14—C15—H15121.1
N1—C2—C1110.46 (13)C7—C16—C17104.65 (13)
N2—C3—N1117.43 (14)C7—C16—H16A110.8
N2—C3—S1130.89 (13)C17—C16—H16A110.8
N1—C3—S1111.62 (12)C7—C16—H16B110.8
N1—C4—C599.92 (13)C17—C16—H16B110.8
N1—C4—H4A111.8H16A—C16—H16B108.9
C5—C4—H4A111.8C18—C17—C16104.10 (15)
N1—C4—H4B111.8C18—C17—H17A110.9
C5—C4—H4B111.8C16—C17—H17A110.9
H4A—C4—H4B109.5C18—C17—H17B110.9
N2—C5—C4107.58 (13)C16—C17—H17B110.9
N2—C5—H5A110.2H17A—C17—H17B109.0
C4—C5—H5A110.2N4—C18—C17101.57 (14)
N2—C5—H5B110.2N4—C18—H18A111.5
C4—C5—H5B110.2C17—C18—H18A111.5
H5A—C5—H5B108.5N4—C18—H18B111.5
C19—C6—C1117.03 (14)C17—C18—H18B111.5
C19—C6—C7113.84 (13)H18A—C18—H18B109.3
C1—C6—C7105.08 (12)C24—C19—C20116.04 (16)
C19—C6—H6106.8C24—C19—C6121.04 (15)
C1—C6—H6106.8C20—C19—C6122.91 (15)
C7—C6—H6106.8C21—C20—C19122.76 (17)
N4—C7—C16105.48 (14)C21—C20—Cl1117.18 (13)
N4—C7—C6105.24 (12)C19—C20—Cl1120.06 (14)
C16—C7—C6113.85 (13)C20—C21—C22119.36 (17)
N4—C7—H7110.7C20—C21—H21120.3
C16—C7—H7110.7C22—C21—H21120.3
C6—C7—H7110.7C21—C22—C23119.26 (18)
N4—C8—C11116.83 (14)C21—C22—H22120.4
N4—C8—C9108.11 (12)C23—C22—H22120.4
C11—C8—C9101.84 (12)C24—C23—C22120.37 (17)
N4—C8—C1106.18 (12)C24—C23—H23119.8
C11—C8—C1115.78 (12)C22—C23—H23119.8
C9—C8—C1107.48 (13)C23—C24—C19122.21 (16)
O2—C9—N3126.81 (15)C23—C24—H24118.9
O2—C9—C8125.72 (14)C19—C24—H24118.9
C3—S1—C1—C217.34 (11)C2—C1—C8—C9−139.50 (13)
C3—S1—C1—C6141.23 (11)C6—C1—C8—C9101.38 (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—O118.2 (3)C10—N3—C9—C83.48 (18)
C3—N1—C2—C18.4 (2)N4—C8—C9—O252.9 (2)
C4—N1—C2—C1−159.95 (16)C11—C8—C9—O2176.57 (16)
C6—C1—C2—O137.6 (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—O1164.42 (14)C11—C8—C9—N3−4.24 (16)
C6—C1—C2—N1−144.15 (14)C1—C8—C9—N3117.90 (14)
C8—C1—C2—N1101.94 (15)C9—N3—C10—C15176.92 (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—C120.1 (2)
C5—N2—C3—S1175.10 (13)N3—C10—C11—C12178.33 (14)
C2—N1—C3—N2−176.64 (14)C15—C10—C11—C8179.98 (14)
C4—N1—C3—N2−5.6 (2)N3—C10—C11—C8−1.82 (18)
C2—N1—C3—S15.81 (19)N4—C8—C11—C12−59.1 (2)
C4—N1—C3—S1176.82 (11)C9—C8—C11—C12−176.61 (17)
C1—S1—C3—N2168.82 (16)C1—C8—C11—C1267.1 (2)
C1—S1—C3—N1−14.05 (12)N4—C8—C11—C10121.09 (14)
C2—N1—C4—C5178.86 (16)C9—C8—C11—C103.57 (16)
C3—N1—C4—C59.66 (16)C1—C8—C11—C10−112.67 (15)
C3—N2—C5—C48.22 (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—C19107.20 (16)C11—C12—C13—C140.0 (3)
C8—C1—C6—C19−135.39 (13)C12—C13—C14—C150.1 (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—C140.0 (2)
C8—C1—C6—C7−7.99 (15)C13—C14—C15—C10−0.2 (3)
S1—C1—C6—C7114.32 (12)N4—C7—C16—C175.22 (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—C1820.32 (18)
C8—N4—C7—C6−37.75 (15)C8—N4—C18—C17163.22 (14)
C18—N4—C7—C690.59 (14)C7—N4—C18—C1742.69 (16)
C19—C6—C7—N4156.75 (13)C16—C17—C18—N4−38.17 (17)
C1—C6—C7—N427.44 (16)C1—C6—C19—C2476.18 (19)
C19—C6—C7—C16−88.23 (17)C7—C6—C19—C24−46.8 (2)
C1—C6—C7—C16142.45 (14)C1—C6—C19—C20−104.47 (18)
C7—N4—C8—C11163.22 (13)C7—C6—C19—C20132.52 (16)
C18—N4—C8—C1143.02 (19)C24—C19—C20—C210.2 (2)
C7—N4—C8—C9−82.74 (14)C6—C19—C20—C21−179.17 (15)
C18—N4—C8—C9157.06 (14)C24—C19—C20—Cl1−179.45 (12)
C7—N4—C8—C132.35 (15)C6—C19—C20—Cl11.2 (2)
C18—N4—C8—C1−87.84 (16)C19—C20—C21—C22−0.4 (3)
C2—C1—C8—N4104.98 (14)Cl1—C20—C21—C22179.24 (13)
C6—C1—C8—N4−14.14 (15)C20—C21—C22—C230.6 (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—C190.3 (3)
C6—C1—C8—C11−145.59 (13)C20—C19—C24—C23−0.1 (2)
S1—C1—C8—C1188.80 (14)C6—C19—C24—C23179.24 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H1···N2i0.88 (2)2.10 (2)2.971 (2)170 (2)

Symmetry codes: (i) −x+1, −y, −z.

Footnotes

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. [PubMed]
  • 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. [PubMed]

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