(Z)-N-{3-[(2-Chloro-1,3-thia-zol-5-yl)meth-yl]-1,3-thia-zolidin-2-yl-idene}cyanamide.

In the title compound, C(8)H(7)ClN(4)S(2), the thia-zole ring is essentially planar [r.m.s. deviation = 0.0011 (2) Å] and conformation of the thia-zolidine ring is twisted on the C-C bond. The C=N bond has a Z configuration.

Related literature

The title compound was synthesized as an inter­mediate for the preparation of pesticides. For the biological activity of this class of compounds, see: Zhang et al. (2000 ▶); Kagabu et al. (2008 ▶). For the synthesis, see: Kozo et al. (1987 ▶); Zuo et al. (2008 ▶). For a related structure. see Li et al. (2010 ▶).

Experimental

Crystal data

C8H7ClN4S2

M = 258.75

Monoclinic,

a = 9.6331 (12) Å

b = 11.2657 (14) Å

c = 10.7675 (13) Å

β = 112.433 (2)°

V = 1080.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.71 mm−1

T = 273 K

0.15 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.901, T max = 0.932

6191 measured reflections

2440 independent reflections

2075 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.108

S = 0.98

2440 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811047404/lh5358sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811047404/lh5358Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047404/lh5358Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811047404/lh5358Isup4.cml

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

C8H7ClN4S2	F(000) = 528
Mr = 258.75	Dx = 1.591 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3349 reflections
a = 9.6331 (12) Å	θ = 2.7–27.5°
b = 11.2657 (14) Å	µ = 0.71 mm−1
c = 10.7675 (13) Å	T = 273 K
β = 112.433 (2)°	Block, colorless
V = 1080.1 (2) Å3	0.15 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	2440 independent reflections
Radiation source: fine-focus sealed tube	2075 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.901, Tmax = 0.932	k = −11→14
6191 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.5077P] where P = (Fo2 + 2Fc2)/3
2440 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.27 e Å−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	0.22859 (6)	0.11411 (5)	0.45559 (5)	0.04850 (16)
S2	0.42112 (6)	0.16077 (5)	0.07049 (5)	0.04881 (17)
Cl1	0.30959 (8)	0.27500 (7)	−0.19805 (6)	0.0715 (2)
N1	0.3166 (2)	−0.00659 (14)	0.29672 (16)	0.0445 (4)
C4	0.3566 (2)	0.02118 (18)	0.08619 (19)	0.0452 (4)
C2	0.3576 (2)	0.08458 (16)	0.38105 (18)	0.0398 (4)
C3	0.4033 (3)	−0.0430 (2)	0.2174 (2)	0.0532 (5)
H3A	0.3906	−0.1277	0.2004	0.064*
H3B	0.5090	−0.0282	0.2688	0.064*
C1	0.1211 (3)	−0.0170 (2)	0.3809 (3)	0.0680 (7)
H1A	0.1433	−0.0804	0.4466	0.082*
H1B	0.0144	0.0000	0.3481	0.082*
N2	0.4818 (2)	0.14397 (16)	0.40261 (18)	0.0485 (4)
C6	0.3112 (2)	0.1563 (2)	−0.09762 (19)	0.0475 (5)
N3	0.2328 (2)	0.0626 (2)	−0.14132 (17)	0.0598 (5)
C8	0.5191 (2)	0.22657 (19)	0.4975 (2)	0.0484 (5)
N4	0.5597 (3)	0.29942 (19)	0.5786 (2)	0.0680 (6)
C7	0.1657 (3)	−0.05279 (19)	0.2663 (2)	0.0527 (5)
H7A	0.1649	−0.1385	0.2579	0.063*
H7B	0.0961	−0.0197	0.1824	0.063*
C5	0.2592 (3)	−0.0145 (2)	−0.0353 (2)	0.0580 (6)
H5A	0.2118	−0.0880	−0.0471	0.070*

	U11	U22	U33	U12	U13	U23
S1	0.0521 (3)	0.0483 (3)	0.0467 (3)	0.0000 (2)	0.0207 (2)	−0.0068 (2)
S2	0.0445 (3)	0.0554 (3)	0.0384 (3)	−0.0010 (2)	0.0067 (2)	−0.0027 (2)
Cl1	0.0720 (4)	0.0877 (5)	0.0533 (3)	0.0002 (3)	0.0224 (3)	0.0209 (3)
N1	0.0568 (10)	0.0397 (8)	0.0339 (7)	0.0054 (7)	0.0139 (7)	−0.0003 (6)
C4	0.0520 (11)	0.0470 (10)	0.0371 (9)	0.0097 (8)	0.0176 (8)	−0.0041 (8)
C2	0.0474 (10)	0.0364 (9)	0.0315 (8)	0.0081 (7)	0.0104 (7)	0.0059 (7)
C3	0.0686 (14)	0.0465 (11)	0.0433 (10)	0.0187 (10)	0.0200 (10)	0.0000 (9)
C1	0.0731 (16)	0.0668 (15)	0.0673 (15)	−0.0213 (13)	0.0304 (13)	−0.0164 (12)
N2	0.0487 (9)	0.0484 (9)	0.0476 (9)	0.0013 (7)	0.0174 (8)	0.0004 (8)
C6	0.0418 (10)	0.0644 (13)	0.0353 (9)	0.0028 (9)	0.0137 (8)	0.0014 (9)
N3	0.0615 (11)	0.0772 (13)	0.0347 (8)	−0.0110 (10)	0.0114 (8)	−0.0067 (9)
C8	0.0432 (10)	0.0453 (11)	0.0526 (11)	−0.0015 (8)	0.0139 (9)	0.0059 (9)
N4	0.0686 (13)	0.0557 (12)	0.0721 (13)	−0.0149 (10)	0.0185 (11)	−0.0115 (10)
C7	0.0626 (13)	0.0431 (10)	0.0436 (10)	−0.0065 (9)	0.0105 (9)	−0.0029 (9)
C5	0.0721 (14)	0.0561 (13)	0.0446 (11)	−0.0100 (11)	0.0210 (10)	−0.0122 (10)

S1—C2	1.749 (2)	C3—H3B	0.9700
S1—C1	1.807 (2)	C1—C7	1.508 (3)
S2—C6	1.714 (2)	C1—H1A	0.9700
S2—C4	1.723 (2)	C1—H1B	0.9700
Cl1—C6	1.716 (2)	N2—C8	1.326 (3)
N1—C2	1.327 (2)	C6—N3	1.279 (3)
N1—C7	1.459 (3)	N3—C5	1.378 (3)
N1—C3	1.463 (3)	C8—N4	1.153 (3)
C4—C5	1.348 (3)	C7—H7A	0.9700
C4—C3	1.495 (3)	C7—H7B	0.9700
C2—N2	1.313 (3)	C5—H5A	0.9300
C3—H3A	0.9700
C2—S1—C1	91.54 (11)	S1—C1—H1A	110.4
C6—S2—C4	88.65 (10)	C7—C1—H1B	110.4
C2—N1—C7	116.13 (17)	S1—C1—H1B	110.4
C2—N1—C3	121.99 (18)	H1A—C1—H1B	108.6
C7—N1—C3	120.70 (17)	C2—N2—C8	117.03 (18)
C5—C4—C3	128.3 (2)	N3—C6—S2	116.92 (17)
C5—C4—S2	108.70 (17)	N3—C6—Cl1	123.34 (16)
C3—C4—S2	123.00 (16)	S2—C6—Cl1	119.75 (13)
N2—C2—N1	121.90 (18)	C6—N3—C5	108.62 (18)
N2—C2—S1	125.56 (15)	N4—C8—N2	175.7 (2)
N1—C2—S1	112.54 (15)	N1—C7—C1	106.93 (17)
N1—C3—C4	112.53 (17)	N1—C7—H7A	110.3
N1—C3—H3A	109.1	C1—C7—H7A	110.3
C4—C3—H3A	109.1	N1—C7—H7B	110.3
N1—C3—H3B	109.1	C1—C7—H7B	110.3
C4—C3—H3B	109.1	H7A—C7—H7B	108.6
H3A—C3—H3B	107.8	C4—C5—N3	117.1 (2)
C7—C1—S1	106.81 (17)	C4—C5—H5A	121.4
C7—C1—H1A	110.4	N3—C5—H5A	121.4
C6—S2—C4—C5	−0.26 (17)	N1—C2—N2—C8	−174.14 (18)
C6—S2—C4—C3	−178.81 (18)	S1—C2—N2—C8	6.2 (3)
C7—N1—C2—N2	−170.80 (17)	C4—S2—C6—N3	0.15 (19)
C3—N1—C2—N2	−3.1 (3)	C4—S2—C6—Cl1	179.78 (14)
C7—N1—C2—S1	8.9 (2)	S2—C6—N3—C5	0.0 (3)
C3—N1—C2—S1	176.56 (14)	Cl1—C6—N3—C5	−179.61 (17)
C1—S1—C2—N2	−174.02 (19)	C2—N1—C7—C1	−22.8 (2)
C1—S1—C2—N1	6.31 (16)	C3—N1—C7—C1	169.36 (19)
C2—N1—C3—C4	−88.0 (2)	S1—C1—C7—N1	25.2 (2)
C7—N1—C3—C4	79.1 (2)	C3—C4—C5—N3	178.8 (2)
C5—C4—C3—N1	−95.7 (3)	S2—C4—C5—N3	0.3 (3)
S2—C4—C3—N1	82.6 (2)	C6—N3—C5—C4	−0.2 (3)
C2—S1—C1—C7	−18.40 (19)