PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2145.
Published online 2008 October 18. doi:  10.1107/S1600536808032984
PMCID: PMC2959598

(E)-Ethyl 2-cyano-2-(thia­zolidin-2-yl­idene)acetate

Abstract

The title compound, C8H10N2O2S, was prepared by the reaction of 2-cyano-3,3-bis­(methyl­sulfan­yl)acrylate and 2-amino­ethanethiol at 350 K. The mol­ecular structure and packing are stabilized by N—H(...)O hydrogen-bond inter­actions. All the non-H atoms are nearly in the same plane with the maximum deviation being 0.08 Å.

Related literature

For biological properties of compounds containing thia­zolidine groups, see: Huang & Shi (1990 [triangle]); Iwata et al. (1988 [triangle]). For related compounds, see: Schroth et al. (1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2145-scheme1.jpg

Experimental

Crystal data

  • C8H10N2O2S
  • M r = 198.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2145-efi1.jpg
  • a = 4.0676 (8) Å
  • b = 15.460 (3) Å
  • c = 14.581 (3) Å
  • β = 90.03 (3)°
  • V = 916.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.32 mm−1
  • T = 293 (2) K
  • 0.20 × 0.12 × 0.09 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 6717 measured reflections
  • 1577 independent reflections
  • 1484 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.112
  • S = 1.24
  • 1577 reflections
  • 119 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032984/at2647sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032984/at2647Isup2.hkl

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

supplementary crystallographic information

Comment

Thiazolidine is an important kind of group in organic chemistry. Many compounds containing thiazolidine groups possess a broad spectrum of biological activities (Iwata et al., 1988; Huang & Shi, 1990). Here, we report the crystal structure of the title compound (I).

In the crystal structure of (I) (Fig. 1), the torsion angle formed by the N1, C3, S1 and C1 is 4.5 (3)°. All the non-H atoms are nearly the same plane with the maximum deviation of atoms being 0.08 Å. The C—S bond lengths of 1.745 (3) and 1.806 (3) Å are in agreement with those observed before (Schroth et al., 1997). In the crystal structure, there are N—H···O hydrogen-bond interactions to stabilize the crystal structure (Table 12).

Experimental

A mixture of ethyl 2-cyano-3,3-bis(methylthio)acrylate 4 mmol (0.87 g) and 2-amino-ethanethiol (0.32 g, 4.1 mmol) is refluxed in absolute EtOH (25 ml) for 4 h. On cooling, the product crystallized and is filtered, and recrystallized from absolute EtOH [yield 0.67 g (85%)]. 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 N—H and C—H distances of 0.86 and 0.93–0.96 Å, respectively, and with Uiso(H) = 1.2 or 1.5Ueq 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 30% probability level.

Crystal data

C8H10N2O2SF(000) = 416
Mr = 198.24Dx = 1.436 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2422 reflections
a = 4.0676 (8) Åθ = 2.3–25.1°
b = 15.460 (3) ŵ = 0.32 mm1
c = 14.581 (3) ÅT = 293 K
β = 90.03 (3)°Needle, colourless
V = 916.9 (3) Å30.20 × 0.12 × 0.09 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1484 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
graphiteθmax = 25.0°, θmin = 3.1°
[var phi] and ω scansh = −4→4
6717 measured reflectionsk = −18→18
1577 independent reflectionsl = −17→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.112w = 1/[σ2(Fo2) + 2.059P] where P = (Fo2 + 2Fc2)/3
S = 1.24(Δ/σ)max < 0.001
1577 reflectionsΔρmax = 0.26 e Å3
119 parametersΔρmin = −0.33 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: 0.041 (3)

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
S10.2265 (2)0.70109 (5)0.01523 (5)0.0285 (3)
O2−0.2856 (6)0.91026 (13)0.24156 (14)0.0250 (5)
O1−0.1022 (6)0.97114 (14)0.11080 (15)0.0325 (6)
N2−0.1952 (7)0.68892 (17)0.23236 (18)0.0304 (7)
N10.1928 (7)0.86360 (17)−0.01208 (17)0.0279 (7)
H1A0.14400.9171−0.00370.034*
C30.1091 (7)0.80489 (19)0.0489 (2)0.0209 (6)
C6−0.1433 (8)0.9071 (2)0.1582 (2)0.0226 (7)
C7−0.3933 (9)0.9959 (2)0.2710 (2)0.0270 (7)
H7A−0.55821.01820.22910.032*
H7B−0.20881.03560.27170.032*
C10.3729 (10)0.7390 (2)−0.0946 (2)0.0337 (8)
H1B0.59460.7182−0.10530.040*
H1C0.23240.7174−0.14330.040*
C4−0.0547 (8)0.82003 (19)0.13177 (19)0.0213 (7)
C5−0.1330 (7)0.7482 (2)0.18828 (19)0.0220 (7)
C20.3686 (8)0.8366 (2)−0.0937 (2)0.0263 (7)
H2A0.59140.8590−0.09260.032*
H2B0.25930.8584−0.14810.032*
C8−0.5358 (9)0.9868 (2)0.3661 (2)0.0330 (8)
H8A−0.60971.04230.38730.049*
H8B−0.37030.96500.40690.049*
H8C−0.71800.94740.36450.049*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0436 (5)0.0177 (4)0.0241 (4)0.0040 (4)0.0121 (3)0.0002 (3)
O20.0389 (13)0.0167 (10)0.0192 (10)0.0020 (9)0.0100 (9)−0.0013 (8)
O10.0527 (15)0.0197 (11)0.0251 (12)0.0021 (11)0.0141 (11)0.0033 (9)
N20.0444 (17)0.0255 (14)0.0215 (14)0.0008 (13)0.0075 (12)0.0017 (12)
N10.0421 (17)0.0182 (13)0.0234 (14)0.0058 (12)0.0128 (12)0.0028 (10)
C30.0237 (15)0.0194 (14)0.0197 (15)0.0003 (13)−0.0012 (12)0.0001 (12)
C60.0272 (17)0.0223 (16)0.0183 (14)−0.0010 (13)0.0039 (12)−0.0021 (12)
C70.0385 (19)0.0182 (15)0.0244 (16)0.0012 (14)0.0057 (14)−0.0035 (12)
C10.051 (2)0.0258 (17)0.0245 (17)0.0088 (16)0.0135 (15)0.0034 (13)
C40.0274 (16)0.0180 (15)0.0183 (14)−0.0005 (13)0.0030 (12)0.0010 (11)
C50.0254 (16)0.0240 (16)0.0166 (14)0.0029 (13)0.0033 (12)−0.0030 (12)
C20.0312 (17)0.0266 (17)0.0212 (15)0.0000 (14)0.0076 (13)0.0001 (13)
C80.045 (2)0.0264 (17)0.0275 (17)0.0059 (16)0.0109 (15)−0.0042 (13)

Geometric parameters (Å, °)

S1—C31.745 (3)C7—C81.510 (4)
S1—C11.806 (3)C7—H7A0.9700
O2—C61.348 (3)C7—H7B0.9700
O2—C71.459 (4)C1—C21.510 (4)
O1—C61.218 (4)C1—H1B0.9700
N2—C51.147 (4)C1—H1C0.9700
N1—C31.315 (4)C4—C51.420 (4)
N1—C21.450 (4)C2—H2A0.9700
N1—H1A0.8600C2—H2B0.9700
C3—C41.400 (4)C8—H8A0.9600
C6—O11.218 (4)C8—H8B0.9600
C6—C41.446 (4)C8—H8C0.9600
C3—S1—C192.39 (14)S1—C1—H1B110.1
C6—O2—C7115.3 (2)C2—C1—H1C110.1
C3—N1—C2119.0 (3)S1—C1—H1C110.1
C3—N1—H1A120.5H1B—C1—H1C108.4
C2—N1—H1A120.5C3—C4—C5118.5 (3)
N1—C3—C4126.3 (3)C3—C4—C6120.3 (3)
N1—C3—S1111.9 (2)C5—C4—C6121.2 (3)
C4—C3—S1121.8 (2)N2—C5—C4178.5 (3)
O1—C6—O2122.8 (3)N1—C2—C1107.5 (2)
O1—C6—O2122.8 (3)N1—C2—H2A110.2
O1—C6—C4124.8 (3)C1—C2—H2A110.2
O1—C6—C4124.8 (3)N1—C2—H2B110.2
O2—C6—C4112.4 (3)C1—C2—H2B110.2
O2—C7—C8107.5 (2)H2A—C2—H2B108.5
O2—C7—H7A110.2C7—C8—H8A109.5
C8—C7—H7A110.2C7—C8—H8B109.5
O2—C7—H7B110.2H8A—C8—H8B109.5
C8—C7—H7B110.2C7—C8—H8C109.5
H7A—C7—H7B108.5H8A—C8—H8C109.5
C2—C1—S1108.2 (2)H8B—C8—H8C109.5
C2—C1—H1B110.1
C2—N1—C3—C4178.7 (3)S1—C3—C4—C5−1.6 (4)
C2—N1—C3—S1−1.4 (4)N1—C3—C4—C6−1.1 (5)
C1—S1—C3—N1−4.5 (3)S1—C3—C4—C6178.9 (2)
C1—S1—C3—C4175.4 (3)O1—C6—C4—C34.2 (5)
O1—O1—C6—O20.0 (3)O1—C6—C4—C34.2 (5)
O1—O1—C6—C40.0 (3)O2—C6—C4—C3−177.2 (3)
C7—O2—C6—O11.0 (4)O1—C6—C4—C5−175.3 (3)
C7—O2—C6—O11.0 (4)O1—C6—C4—C5−175.3 (3)
C7—O2—C6—C4−177.6 (3)O2—C6—C4—C53.3 (4)
C6—O2—C7—C8−178.4 (3)C3—N1—C2—C18.0 (4)
C3—S1—C1—C28.7 (3)S1—C1—C2—N1−10.3 (4)
N1—C3—C4—C5178.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.862.332.955 (3)129
N1—H1A···O10.862.122.723 (3)127

Symmetry codes: (i) −x, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2647).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Huang, Z. T. & Shi, X. (1990). Synthesis, pp. 162–167.
  • Iwata, C., Watanabe, M., Okamoto, S., Fujimoto, M., Sakae, M., Katstrada, M. & Imanishi, T. (1988). Synthesis, pp. 261–262.
  • 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]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography