{3-[(2-Chloro-1,3-thia-zol-4-yl)meth-yl]-1,3-thia-zolidin-2-yl-idene-amino}-formonitrile.

In the title compound, C(8)H(7)ClN(4)S(2), the dihedral angle between the thia-zolidine ring (r.m.s. deviation = 0.028 Å) and the thia-zole ring (r.m.s. deviation = 0.004 Å) is 74.74 (6)°. The formonitrile group is almost coplanar with the attached ring [C-N-C-N torsion angle = 167 (2)°.

Related literature

For the biological activity of compounds containing a thia­zole ring, see: Ehrenfreund et al. (2003 ▶); Kim et al. (2002 ▶); Maienfisch & Gsell (1998 ▶); Shiga et al. (2003 ▶); Smith & Hunter (2001 ▶); Tanaka et al. (2005 ▶). For the bioactivity of 1,3-thia­zolidine derivatives, see: Albrecht et al. (2005 ▶); Liu & Li (2000 ▶); Ueda et al. (2004 ▶); Yeh & Chen (2002 ▶).

Experimental

Crystal data

C8H7ClN4S2

M = 258.75

Monoclinic,

a = 6.1731 (9) Å

b = 16.807 (2) Å

c = 10.9057 (14) Å

β = 105.846 (2)°

V = 1088.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 294 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.860, T max = 0.884

6141 measured reflections

2220 independent reflections

1862 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.103

S = 1.05

2220 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536810035579/ci5173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035579/ci5173Isup2.hkl

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

C8H7ClN4S2	F(000) = 528
Mr = 258.75	Dx = 1.579 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3431 reflections
a = 6.1731 (9) Å	θ = 2.4–26.2°
b = 16.807 (2) Å	µ = 0.70 mm−1
c = 10.9057 (14) Å	T = 294 K
β = 105.846 (2)°	Monoclinic, colourless
V = 1088.5 (3) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2220 independent reflections
Radiation source: fine-focus sealed tube	1862 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.860, Tmax = 0.884	k = −15→21
6141 measured reflections	l = −11→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.3256P] where P = (Fo2 + 2Fc2)/3
2220 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.34 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
Cl1	−0.27073 (11)	0.02267 (4)	0.65605 (6)	0.0705 (2)
S1	0.70384 (10)	0.09234 (4)	1.21031 (5)	0.0588 (2)
S2	0.07788 (10)	0.10824 (3)	0.56567 (5)	0.05097 (18)
N1	0.4957 (3)	0.15672 (9)	0.99768 (14)	0.0389 (4)
N2	0.3327 (3)	0.18765 (11)	1.15862 (15)	0.0466 (4)
N3	0.3408 (4)	0.18457 (14)	1.38596 (19)	0.0669 (6)
N4	0.0452 (3)	0.11665 (10)	0.79535 (15)	0.0410 (4)
C1	0.8149 (4)	0.07222 (18)	1.0769 (2)	0.0660 (7)
H1A	0.9724	0.0873	1.0975	0.079*
H1B	0.8034	0.0159	1.0571	0.079*
C2	0.6843 (4)	0.11841 (17)	0.9667 (2)	0.0631 (7)
H2A	0.7801	0.1583	0.9440	0.076*
H2B	0.6296	0.0834	0.8942	0.076*
C3	0.4872 (3)	0.15132 (11)	1.11773 (17)	0.0370 (4)
C4	0.3448 (4)	0.18300 (13)	1.2819 (2)	0.0478 (5)
C5	0.3492 (3)	0.20877 (12)	0.90364 (17)	0.0426 (4)
H5A	0.4394	0.2499	0.8790	0.051*
H5B	0.2428	0.2346	0.9417	0.051*
C6	0.2233 (3)	0.16430 (11)	0.78796 (17)	0.0378 (4)
C7	0.2661 (4)	0.16624 (12)	0.67255 (17)	0.0451 (5)
H7	0.3818	0.1951	0.6541	0.054*
C8	−0.0433 (3)	0.08538 (11)	0.68491 (19)	0.0428 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0659 (4)	0.0730 (4)	0.0743 (4)	−0.0187 (3)	0.0221 (3)	−0.0253 (3)
S1	0.0642 (4)	0.0707 (4)	0.0407 (3)	0.0175 (3)	0.0133 (3)	0.0086 (3)
S2	0.0674 (4)	0.0577 (3)	0.0290 (3)	0.0066 (3)	0.0152 (2)	−0.0030 (2)
N1	0.0391 (8)	0.0492 (9)	0.0307 (8)	0.0022 (7)	0.0131 (6)	−0.0022 (7)
N2	0.0483 (9)	0.0586 (10)	0.0382 (9)	0.0007 (8)	0.0208 (7)	−0.0049 (7)
N3	0.0869 (15)	0.0758 (14)	0.0499 (11)	−0.0106 (11)	0.0390 (11)	−0.0082 (10)
N4	0.0470 (9)	0.0462 (9)	0.0335 (8)	0.0025 (7)	0.0174 (7)	−0.0024 (7)
C1	0.0546 (13)	0.0878 (18)	0.0591 (14)	0.0197 (13)	0.0218 (11)	0.0030 (13)
C2	0.0664 (15)	0.0811 (17)	0.0517 (13)	0.0266 (13)	0.0328 (12)	0.0063 (12)
C3	0.0369 (9)	0.0420 (10)	0.0328 (9)	−0.0068 (8)	0.0108 (7)	−0.0030 (7)
C4	0.0526 (12)	0.0519 (12)	0.0465 (12)	−0.0061 (9)	0.0264 (9)	−0.0056 (9)
C5	0.0517 (11)	0.0417 (10)	0.0356 (9)	0.0012 (8)	0.0140 (8)	−0.0005 (8)
C6	0.0448 (10)	0.0398 (10)	0.0310 (9)	0.0074 (8)	0.0141 (7)	0.0027 (7)
C7	0.0549 (12)	0.0498 (11)	0.0345 (10)	0.0026 (9)	0.0191 (9)	0.0019 (8)
C8	0.0470 (10)	0.0435 (10)	0.0397 (10)	0.0051 (8)	0.0149 (8)	−0.0041 (8)

Cl1—C8	1.715 (2)	N4—C6	1.380 (2)
S1—C3	1.7471 (19)	C1—C2	1.472 (3)
S1—C1	1.801 (2)	C1—H1A	0.97
S2—C7	1.709 (2)	C1—H1B	0.97
S2—C8	1.711 (2)	C2—H2A	0.97
N1—C3	1.328 (2)	C2—H2B	0.97
N1—C2	1.448 (3)	C5—C6	1.490 (3)
N1—C5	1.459 (2)	C5—H5A	0.97
N2—C3	1.309 (2)	C5—H5B	0.97
N2—C4	1.328 (3)	C6—C7	1.355 (3)
N3—C4	1.142 (3)	C7—H7	0.93
N4—C8	1.291 (2)
C3—S1—C1	92.29 (10)	N2—C3—N1	122.18 (17)
C7—S2—C8	88.08 (10)	N2—C3—S1	125.57 (14)
C3—N1—C2	116.74 (17)	N1—C3—S1	112.25 (14)
C3—N1—C5	123.40 (16)	N3—C4—N2	173.6 (3)
C2—N1—C5	119.09 (15)	N1—C5—C6	111.98 (15)
C3—N2—C4	118.19 (18)	N1—C5—H5A	109.2
C8—N4—C6	108.81 (16)	C6—C5—H5A	109.2
C2—C1—S1	108.40 (16)	N1—C5—H5B	109.2
C2—C1—H1A	110.0	C6—C5—H5B	109.2
S1—C1—H1A	110.0	H5A—C5—H5B	107.9
C2—C1—H1B	110.0	C7—C6—N4	115.37 (17)
S1—C1—H1B	110.0	C7—C6—C5	125.85 (19)
H1A—C1—H1B	108.4	N4—C6—C5	118.78 (16)
N1—C2—C1	109.89 (18)	C6—C7—S2	110.57 (16)
N1—C2—H2A	109.7	C6—C7—H7	124.7
C1—C2—H2A	109.7	S2—C7—H7	124.7
N1—C2—H2B	109.7	N4—C8—S2	117.15 (16)
C1—C2—H2B	109.7	N4—C8—Cl1	122.55 (16)
H2A—C2—H2B	108.2	S2—C8—Cl1	120.29 (12)
C3—S1—C1—C2	4.2 (2)	C3—N1—C5—C6	−124.90 (19)
C3—N1—C2—C1	6.9 (3)	C2—N1—C5—C6	65.5 (2)
C5—N1—C2—C1	177.2 (2)	C8—N4—C6—C7	−1.2 (2)
S1—C1—C2—N1	−6.7 (3)	C8—N4—C6—C5	178.42 (17)
C4—N2—C3—N1	−175.95 (18)	N1—C5—C6—C7	−106.0 (2)
C4—N2—C3—S1	3.3 (3)	N1—C5—C6—N4	74.4 (2)
C2—N1—C3—N2	175.7 (2)	N4—C6—C7—S2	0.9 (2)
C5—N1—C3—N2	5.9 (3)	C5—C6—C7—S2	−178.68 (15)
C2—N1—C3—S1	−3.7 (2)	C8—S2—C7—C6	−0.28 (16)
C5—N1—C3—S1	−173.46 (14)	C6—N4—C8—S2	1.0 (2)
C1—S1—C3—N2	−179.83 (19)	C6—N4—C8—Cl1	−179.65 (14)
C1—S1—C3—N1	−0.49 (17)	C7—S2—C8—N4	−0.42 (17)
C3—N2—C4—N3	167 (2)	C7—S2—C8—Cl1	−179.83 (14)