(E)-Ethyl 2-cyano-2-(thia-zolidin-2-yl-idene)acetate.

The title compound, C(8)H(10)N(2)O(2)S, was prepared by the reaction of 2-cyano-3,3-bis-(methyl-sulfan-yl)acrylate and 2-amino-ethanethiol at 350 K. The mol-ecular structure and packing are stabilized by N-H⋯O hydrogen-bond inter-actions. 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 ▶); Iwata et al. (1988 ▶). For related compounds, see: Schroth et al. (1997 ▶).

Experimental

Crystal data

C8H10N2O2S

M = 198.24

Monoclinic,

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 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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.

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

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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 code: (i) .