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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2321.
Published online 2008 November 13. doi:  10.1107/S1600536808036568
PMCID: PMC2960110

N-[(Z)-3-(4-Chloro­benzo­yl)-1,3-thia­zolidin-2-yl­idene]cyanamide

Abstract

The title compound, C11H8ClN3OS, was prepared by the reaction of N-cyano­imino­thia­zolidine, 2-amino­ethanethiol and triethyl­amine at 350 K. The dihedral angle between the two rings is 62.5 (8)°.

Related literature

For the biological activities of thia­zolidine compounds, see: Iwata et al. (1988 [triangle]); Huang & Shi (1990 [triangle]). For related structures, see Jian et al. (2006 [triangle]); Schroth et al. (1997 [triangle]).

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Object name is e-64-o2321-scheme1.jpg

Experimental

Crystal data

  • C11H8ClN3OS
  • M r = 265.72
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2321-efi1.jpg
  • a = 16.442 (3) Å
  • b = 5.6798 (11) Å
  • c = 13.313 (3) Å
  • β = 112.76 (3)°
  • V = 1146.5 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.50 mm−1
  • T = 293 (2) K
  • 0.34 × 0.21 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 8343 measured reflections
  • 2016 independent reflections
  • 1915 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.066
  • S = 1.13
  • 2016 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036568/pk2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036568/pk2128Isup2.hkl

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

supplementary crystallographic information

Comment

Thiazolidine is an important group in organic chemistry. Many compounds containing thiazolidine groups possess a broad spectrum of biological activities (Iwata et al., 1988; Huang & Shi, 1990).

In the crystal structure (Fig. 1), the torsion angle formed by atoms N1, C8, C9 and S1 was 34.5 (9)°. The dihedral angle formed by the the ring (N1, C8, C9, C10 and S1) and the phenyl ring (C1-C6) was 62.5 (8)°. The C=N bond length (1.299 (2) Å) is in agreement with that observed before (Jian et al., 2006). The C—S bond length (1.734 (7) and 1.808 (2) Å) are in agreement with those observed before (Schroth et al., 1997). Intermolecular C–H···N interactions help to stabilize the crystal structure.

Experimental

A mixture of N-cyanoiminothiazolidine 10 mmol (1.27 g), 2-amino-ethanethiol (1.75 g, 10 mmol) and (1.01 g, 10 mmol) triethylamine was refluxed in absolute acetone (25 ml) for 4 h. On cooling, the product crystallized, was filtered, and recrystallized from absolute EtOH (yield 2.42 g (91%)). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, respectively, and Uiso(H) = 1.2 Ueq of the parent atoms.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level.

Crystal data

C11H8ClN3OSF000 = 544
Mr = 265.72Dx = 1.539 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1021 reflections
a = 16.442 (3) Åθ = 2.9–26.4º
b = 5.6798 (11) ŵ = 0.50 mm1
c = 13.313 (3) ÅT = 293 (2) K
β = 112.76 (3)ºBlock, colorless
V = 1146.5 (5) Å30.34 × 0.21 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1915 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Monochromator: graphiteθmax = 25.0º
T = 293(2) Kθmin = 3.1º
[var phi] and ω scansh = −19→19
Absorption correction: nonek = −6→6
8343 measured reflectionsl = −15→15
2016 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026  w = 1/[σ2(Fo2) + (0.017P)2 + 0.7287P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.066(Δ/σ)max < 0.001
S = 1.13Δρmax = 0.21 e Å3
2016 reflectionsΔρmin = −0.22 e Å3
155 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.031 (2)
Secondary atom site location: difference Fourier map

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
S10.07965 (3)0.52934 (7)0.33331 (3)0.02469 (14)
Cl10.46689 (3)0.71315 (8)0.06338 (3)0.03512 (15)
O10.27367 (8)1.17756 (19)0.37317 (10)0.0302 (3)
N20.16368 (9)0.5912 (2)0.19639 (11)0.0244 (3)
C30.40564 (10)0.7898 (3)0.13961 (12)0.0229 (3)
N10.20390 (8)0.8283 (2)0.35254 (10)0.0216 (3)
C100.15500 (10)0.6503 (3)0.28595 (12)0.0201 (3)
C40.40148 (10)0.6326 (3)0.21690 (12)0.0232 (3)
H4A0.43150.49010.22810.028*
N30.08333 (10)0.2509 (3)0.08619 (14)0.0426 (4)
C70.26182 (10)0.9843 (3)0.33103 (12)0.0220 (3)
C60.30963 (9)0.9060 (3)0.26219 (12)0.0197 (3)
C80.16984 (11)0.9017 (3)0.43566 (13)0.0263 (4)
H8A0.12701.02720.40770.032*
H8B0.21760.95740.50070.032*
C10.31667 (10)1.0641 (3)0.18625 (13)0.0227 (3)
H1A0.28961.21060.17790.027*
C90.12728 (11)0.6865 (3)0.46101 (13)0.0268 (4)
H9A0.08200.73120.48720.032*
H9B0.17080.59010.51580.032*
C110.11795 (11)0.4075 (3)0.14112 (14)0.0275 (4)
C50.35225 (10)0.6895 (3)0.27740 (12)0.0222 (3)
H5A0.34770.58330.32810.027*
C20.36370 (10)1.0057 (3)0.12284 (13)0.0244 (3)
H2B0.36691.10930.07040.029*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0224 (2)0.0236 (2)0.0314 (2)−0.00304 (16)0.01415 (17)0.00002 (16)
Cl10.0368 (3)0.0412 (3)0.0340 (2)0.00200 (19)0.02096 (19)−0.00607 (19)
O10.0369 (7)0.0210 (6)0.0374 (7)−0.0065 (5)0.0194 (5)−0.0072 (5)
N20.0252 (7)0.0244 (7)0.0252 (7)−0.0060 (6)0.0115 (6)−0.0039 (6)
C30.0187 (7)0.0266 (8)0.0226 (8)−0.0038 (6)0.0071 (6)−0.0060 (6)
N10.0246 (7)0.0207 (7)0.0217 (6)−0.0036 (5)0.0114 (5)−0.0012 (5)
C100.0185 (7)0.0167 (7)0.0243 (8)0.0018 (6)0.0075 (6)0.0039 (6)
C40.0194 (8)0.0190 (7)0.0273 (8)0.0006 (6)0.0047 (6)−0.0016 (6)
N30.0337 (8)0.0427 (10)0.0586 (11)−0.0120 (8)0.0257 (8)−0.0256 (9)
C70.0218 (8)0.0201 (8)0.0229 (8)−0.0012 (6)0.0072 (6)0.0024 (6)
C60.0171 (7)0.0187 (7)0.0219 (7)−0.0047 (6)0.0062 (6)−0.0019 (6)
C80.0293 (8)0.0284 (8)0.0244 (8)−0.0013 (7)0.0140 (7)−0.0026 (7)
C10.0209 (8)0.0171 (7)0.0289 (8)−0.0013 (6)0.0082 (6)0.0017 (6)
C90.0248 (8)0.0326 (9)0.0236 (8)−0.0002 (7)0.0101 (7)0.0028 (7)
C110.0230 (8)0.0303 (9)0.0348 (9)−0.0025 (7)0.0172 (7)−0.0056 (8)
C50.0226 (8)0.0192 (8)0.0227 (8)−0.0029 (6)0.0064 (6)0.0022 (6)
C20.0242 (8)0.0248 (8)0.0245 (8)−0.0030 (7)0.0099 (6)0.0040 (7)

Geometric parameters (Å, °)

S1—C101.7347 (15)N3—C111.152 (2)
S1—C91.8082 (17)C7—C61.488 (2)
Cl1—C31.7390 (16)C6—C11.390 (2)
O1—C71.2136 (19)C6—C51.391 (2)
N2—C101.299 (2)C8—C91.510 (2)
N2—C111.329 (2)C8—H8A0.9700
C3—C21.382 (2)C8—H8B0.9700
C3—C41.384 (2)C1—C21.388 (2)
N1—C101.379 (2)C1—H1A0.9300
N1—C71.409 (2)C9—H9A0.9700
N1—C81.4804 (19)C9—H9B0.9700
C4—C51.383 (2)C5—H5A0.9300
C4—H4A0.9300C2—H2B0.9300
C10—S1—C992.05 (8)N1—C8—H8A110.5
C10—N2—C11118.14 (14)C9—C8—H8A110.5
C2—C3—C4121.83 (14)N1—C8—H8B110.5
C2—C3—Cl1119.55 (12)C9—C8—H8B110.5
C4—C3—Cl1118.61 (12)H8A—C8—H8B108.7
C10—N1—C7127.01 (13)C2—C1—C6120.72 (14)
C10—N1—C8113.06 (12)C2—C1—H1A119.6
C7—N1—C8117.11 (13)C6—C1—H1A119.6
N2—C10—N1122.40 (14)C8—C9—S1105.01 (11)
N2—C10—S1125.37 (12)C8—C9—H9A110.7
N1—C10—S1112.17 (11)S1—C9—H9A110.7
C5—C4—C3119.40 (14)C8—C9—H9B110.7
C5—C4—H4A120.3S1—C9—H9B110.7
C3—C4—H4A120.3H9A—C9—H9B108.8
O1—C7—N1118.36 (14)N3—C11—N2172.67 (18)
O1—C7—C6121.78 (14)C4—C5—C6119.80 (14)
N1—C7—C6119.80 (13)C4—C5—H5A120.1
C1—C6—C5119.87 (14)C6—C5—H5A120.1
C1—C6—C7117.87 (14)C3—C2—C1118.32 (14)
C5—C6—C7122.08 (14)C3—C2—H2B120.8
N1—C8—C9106.32 (13)C1—C2—H2B120.8
C11—N2—C10—N1175.68 (14)N1—C7—C6—C1138.53 (15)
C11—N2—C10—S1−7.2 (2)O1—C7—C6—C5130.83 (17)
C7—N1—C10—N26.7 (2)N1—C7—C6—C5−46.3 (2)
C8—N1—C10—N2167.01 (14)C10—N1—C8—C929.96 (17)
C7—N1—C10—S1−170.72 (12)C7—N1—C8—C9−167.65 (13)
C8—N1—C10—S1−10.44 (16)C5—C6—C1—C21.9 (2)
C9—S1—C10—N2172.92 (14)C7—C6—C1—C2177.18 (14)
C9—S1—C10—N1−9.73 (12)N1—C8—C9—S1−34.60 (15)
C2—C3—C4—C51.7 (2)C10—S1—C9—C825.81 (12)
Cl1—C3—C4—C5−179.26 (11)C3—C4—C5—C6−1.8 (2)
C10—N1—C7—O1152.51 (15)C1—C6—C5—C40.0 (2)
C8—N1—C7—O1−7.1 (2)C7—C6—C5—C4−175.00 (14)
C10—N1—C7—C6−30.2 (2)C4—C3—C2—C10.2 (2)
C8—N1—C7—C6170.18 (13)Cl1—C3—C2—C1−178.80 (12)
O1—C7—C6—C1−44.3 (2)C6—C1—C2—C3−2.1 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2128).

References

  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin.
  • Huang, Z. T. & Shi, X. (1990). Synthesis, 2, 162–167.
  • Iwata, C., Watanabe, M., Okamoto, S., Fujimoto, M., Sakae, M., Katstrada, M. & Imanishi, T. (1988). Synthesis, 3, 261–262.
  • Jian, F.-F., Zhuang, R.-R., Wang, K.-F., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o3198–o3199.
  • Schroth, W., Hintzsche, E., Jordan, H., Jende, T., Spitzner, R. & Thondorf, I. (1997). Tetrahedron, 53, 7509–7528.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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