Acta Cryst. (2008). E64, o2145 [ doi:10.1107/S1600536808032984 ]
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.
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.
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.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./at2647fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
| C8H10N2O2S | F(000) = 416 |
| Mr = 198.24 | Dx = 1.436 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2422 reflections |
| a = 4.0676 (8) Å | θ = 2.3–25.1° |
| b = 15.460 (3) Å | µ = 0.32 mm−1 |
| c = 14.581 (3) Å | T = 293 K |
| β = 90.03 (3)° | Needle, colourless |
| V = 916.9 (3) Å3 | 0.20 × 0.12 × 0.09 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 1484 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.025 |
| graphite | θmax = 25.0°, θmin = 3.1° |
| φ and ω scans | h = −4→4 |
| 6717 measured reflections | k = −18→18 |
| 1577 independent reflections | l = −17→17 |
| 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)] = 0.051 | H-atom parameters constrained |
| wR(F2) = 0.112 | w = 1/[σ2(Fo2) + 2.059P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.24 | (Δ/σ)max < 0.001 |
| 1577 reflections | Δρmax = 0.26 e Å−3 |
| 119 parameters | Δρmin = −0.33 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: 0.041 (3) |
| C8H10N2O2S | V = 916.9 (3) Å3 |
| Mr = 198.24 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 4.0676 (8) Å | µ = 0.32 mm−1 |
| b = 15.460 (3) Å | T = 293 K |
| c = 14.581 (3) Å | 0.20 × 0.12 × 0.09 mm |
| β = 90.03 (3)° |
| Bruker SMART CCD area-detector diffractometer | 1484 reflections with I > 2σ(I) |
| 6717 measured reflections | Rint = 0.025 |
| 1577 independent reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
| wR(F2) = 0.112 | Δρmax = 0.26 e Å−3 |
| S = 1.24 | Δρmin = −0.33 e Å−3 |
| 1577 reflections | Absolute structure: ? |
| 119 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.2265 (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) | |
| N1 | 0.1928 (7) | 0.86360 (17) | −0.01208 (17) | 0.0279 (7) | |
| H1A | 0.1440 | 0.9171 | −0.0037 | 0.034* | |
| C3 | 0.1091 (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 | −0.5582 | 1.0182 | 0.2291 | 0.032* | |
| H7B | −0.2088 | 1.0356 | 0.2717 | 0.032* | |
| C1 | 0.3729 (10) | 0.7390 (2) | −0.0946 (2) | 0.0337 (8) | |
| H1B | 0.5946 | 0.7182 | −0.1053 | 0.040* | |
| H1C | 0.2324 | 0.7174 | −0.1433 | 0.040* | |
| 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) | |
| C2 | 0.3686 (8) | 0.8366 (2) | −0.0937 (2) | 0.0263 (7) | |
| H2A | 0.5914 | 0.8590 | −0.0926 | 0.032* | |
| H2B | 0.2593 | 0.8584 | −0.1481 | 0.032* | |
| C8 | −0.5358 (9) | 0.9868 (2) | 0.3661 (2) | 0.0330 (8) | |
| H8A | −0.6097 | 1.0423 | 0.3873 | 0.049* | |
| H8B | −0.3703 | 0.9650 | 0.4069 | 0.049* | |
| H8C | −0.7180 | 0.9474 | 0.3645 | 0.049* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0436 (5) | 0.0177 (4) | 0.0241 (4) | 0.0040 (4) | 0.0121 (3) | 0.0002 (3) |
| O2 | 0.0389 (13) | 0.0167 (10) | 0.0192 (10) | 0.0020 (9) | 0.0100 (9) | −0.0013 (8) |
| O1 | 0.0527 (15) | 0.0197 (11) | 0.0251 (12) | 0.0021 (11) | 0.0141 (11) | 0.0033 (9) |
| N2 | 0.0444 (17) | 0.0255 (14) | 0.0215 (14) | 0.0008 (13) | 0.0075 (12) | 0.0017 (12) |
| N1 | 0.0421 (17) | 0.0182 (13) | 0.0234 (14) | 0.0058 (12) | 0.0128 (12) | 0.0028 (10) |
| C3 | 0.0237 (15) | 0.0194 (14) | 0.0197 (15) | 0.0003 (13) | −0.0012 (12) | 0.0001 (12) |
| C6 | 0.0272 (17) | 0.0223 (16) | 0.0183 (14) | −0.0010 (13) | 0.0039 (12) | −0.0021 (12) |
| C7 | 0.0385 (19) | 0.0182 (15) | 0.0244 (16) | 0.0012 (14) | 0.0057 (14) | −0.0035 (12) |
| C1 | 0.051 (2) | 0.0258 (17) | 0.0245 (17) | 0.0088 (16) | 0.0135 (15) | 0.0034 (13) |
| C4 | 0.0274 (16) | 0.0180 (15) | 0.0183 (14) | −0.0005 (13) | 0.0030 (12) | 0.0010 (11) |
| C5 | 0.0254 (16) | 0.0240 (16) | 0.0166 (14) | 0.0029 (13) | 0.0033 (12) | −0.0030 (12) |
| C2 | 0.0312 (17) | 0.0266 (17) | 0.0212 (15) | 0.0000 (14) | 0.0076 (13) | 0.0001 (13) |
| C8 | 0.045 (2) | 0.0264 (17) | 0.0275 (17) | 0.0059 (16) | 0.0109 (15) | −0.0042 (13) |
| S1—C3 | 1.745 (3) | C7—C8 | 1.510 (4) |
| S1—C1 | 1.806 (3) | C7—H7A | 0.9700 |
| O2—C6 | 1.348 (3) | C7—H7B | 0.9700 |
| O2—C7 | 1.459 (4) | C1—C2 | 1.510 (4) |
| O1—C6 | 1.218 (4) | C1—H1B | 0.9700 |
| N2—C5 | 1.147 (4) | C1—H1C | 0.9700 |
| N1—C3 | 1.315 (4) | C4—C5 | 1.420 (4) |
| N1—C2 | 1.450 (4) | C2—H2A | 0.9700 |
| N1—H1A | 0.8600 | C2—H2B | 0.9700 |
| C3—C4 | 1.400 (4) | C8—H8A | 0.9600 |
| C6—O1 | 1.218 (4) | C8—H8B | 0.9600 |
| C6—C4 | 1.446 (4) | C8—H8C | 0.9600 |
| C3—S1—C1 | 92.39 (14) | S1—C1—H1B | 110.1 |
| C6—O2—C7 | 115.3 (2) | C2—C1—H1C | 110.1 |
| C3—N1—C2 | 119.0 (3) | S1—C1—H1C | 110.1 |
| C3—N1—H1A | 120.5 | H1B—C1—H1C | 108.4 |
| C2—N1—H1A | 120.5 | C3—C4—C5 | 118.5 (3) |
| N1—C3—C4 | 126.3 (3) | C3—C4—C6 | 120.3 (3) |
| N1—C3—S1 | 111.9 (2) | C5—C4—C6 | 121.2 (3) |
| C4—C3—S1 | 121.8 (2) | N2—C5—C4 | 178.5 (3) |
| O1—C6—O2 | 122.8 (3) | N1—C2—C1 | 107.5 (2) |
| O1—C6—O2 | 122.8 (3) | N1—C2—H2A | 110.2 |
| O1—C6—C4 | 124.8 (3) | C1—C2—H2A | 110.2 |
| O1—C6—C4 | 124.8 (3) | N1—C2—H2B | 110.2 |
| O2—C6—C4 | 112.4 (3) | C1—C2—H2B | 110.2 |
| O2—C7—C8 | 107.5 (2) | H2A—C2—H2B | 108.5 |
| O2—C7—H7A | 110.2 | C7—C8—H8A | 109.5 |
| C8—C7—H7A | 110.2 | C7—C8—H8B | 109.5 |
| O2—C7—H7B | 110.2 | H8A—C8—H8B | 109.5 |
| C8—C7—H7B | 110.2 | C7—C8—H8C | 109.5 |
| H7A—C7—H7B | 108.5 | H8A—C8—H8C | 109.5 |
| C2—C1—S1 | 108.2 (2) | H8B—C8—H8C | 109.5 |
| C2—C1—H1B | 110.1 | ||
| C2—N1—C3—C4 | 178.7 (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—C6 | 178.9 (2) |
| C1—S1—C3—C4 | 175.4 (3) | O1—C6—C4—C3 | 4.2 (5) |
| O1—O1—C6—O2 | 0.0 (3) | O1—C6—C4—C3 | 4.2 (5) |
| O1—O1—C6—C4 | 0.0 (3) | O2—C6—C4—C3 | −177.2 (3) |
| C7—O2—C6—O1 | 1.0 (4) | O1—C6—C4—C5 | −175.3 (3) |
| C7—O2—C6—O1 | 1.0 (4) | O1—C6—C4—C5 | −175.3 (3) |
| C7—O2—C6—C4 | −177.6 (3) | O2—C6—C4—C5 | 3.3 (4) |
| C6—O2—C7—C8 | −178.4 (3) | C3—N1—C2—C1 | 8.0 (4) |
| C3—S1—C1—C2 | 8.7 (3) | S1—C1—C2—N1 | −10.3 (4) |
| N1—C3—C4—C5 | 178.4 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1i | 0.86 | 2.33 | 2.955 (3) | 129 |
| N1—H1A···O1 | 0.86 | 2.12 | 2.723 (3) | 127 |
| Symmetry codes: (i) −x, −y+2, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1i | 0.86 | 2.33 | 2.955 (3) | 129 |
| N1—H1A···O1 | 0.86 | 2.12 | 2.723 (3) | 127 |
| Symmetry codes: (i) −x, −y+2, −z. |
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.
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).