2-Chloro-5-chloro-meth-yl-1,3-thia-zole.

In the title compound, C(4)H(3)Cl(2)NS, the chloro-methyl C and 2-position Cl atoms lie close to the mean plane of the thia-zole ring [deviations = 0.0568 (2) and 0.0092 (1) Å, respectively]. No classical hydrogen bonds are found in the crystal structure.

Related literature

The title compound is an inter­mediate in the manufacture of agrochemicals, see: Kozo et al. (1986 ▶). For the synthesis of the title compound, see: Beck & Heitzer (1988 ▶); For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C4H3Cl2NS

M = 168.03

Monoclinic,

a = 4.2430 (8) Å

b = 17.151 (3) Å

c = 9.1640 (18) Å

β = 96.82 (3)°

V = 662.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.18 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.718, T max = 0.891

2697 measured reflections

1211 independent reflections

932 reflections with I > 2σ(I)

R int = 0.060

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.151

S = 1.00

1211 reflections

74 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 I, global. DOI: 10.1107/S1600536811019052/vm2096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019052/vm2096Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019052/vm2096Isup3.cml

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

C4H3Cl2NS	F(000) = 336
Mr = 168.03	Dx = 1.686 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 4.2430 (8) Å	θ = 10–13°
b = 17.151 (3) Å	µ = 1.18 mm−1
c = 9.1640 (18) Å	T = 293 K
β = 96.82 (3)°	Block, colourless
V = 662.2 (2) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	932 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
graphite	θmax = 25.4°, θmin = 2.4°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = −20→20
Tmin = 0.718, Tmax = 0.891	l = −11→10
2697 measured reflections	3 standard reflections every 200 reflections
1211 independent reflections	intensity decay: 1%

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.098P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1211 reflections	Δρmax = 0.30 e Å−3
74 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (8)

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
S	0.3422 (2)	0.57491 (5)	0.76517 (10)	0.0589 (4)
N	0.5235 (10)	0.71113 (19)	0.8427 (3)	0.0725 (10)
Cl1	0.7424 (3)	0.60986 (7)	1.04471 (11)	0.0811 (5)
C1	0.5381 (9)	0.6400 (2)	0.8830 (3)	0.0530 (9)
Cl2	0.2025 (2)	0.58243 (7)	0.38099 (10)	0.0671 (4)
C2	0.2262 (8)	0.6502 (2)	0.6483 (3)	0.0484 (8)
C3	0.3450 (12)	0.7162 (2)	0.7087 (4)	0.0684 (11)
H3A	0.3078	0.7639	0.6615	0.082*
C4	0.0159 (10)	0.6382 (2)	0.5089 (4)	0.0637 (10)
H4A	−0.0443	0.6886	0.4660	0.076*
H4B	−0.1761	0.6119	0.5297	0.076*

	U11	U22	U33	U12	U13	U23
S	0.0750 (7)	0.0467 (5)	0.0523 (6)	−0.0053 (4)	−0.0033 (4)	0.0014 (4)
N	0.109 (3)	0.0552 (18)	0.0516 (18)	−0.016 (2)	0.0015 (18)	−0.0070 (14)
Cl1	0.0967 (9)	0.0963 (9)	0.0464 (6)	0.0075 (6)	−0.0078 (5)	0.0011 (5)
C1	0.065 (2)	0.055 (2)	0.0386 (17)	−0.0016 (17)	0.0064 (15)	−0.0013 (14)
Cl2	0.0682 (7)	0.0810 (7)	0.0494 (6)	−0.0024 (5)	−0.0041 (4)	−0.0146 (4)
C2	0.0480 (19)	0.0554 (19)	0.0427 (17)	0.0070 (15)	0.0090 (14)	0.0017 (14)
C3	0.102 (3)	0.0468 (19)	0.055 (2)	0.003 (2)	0.005 (2)	0.0037 (17)
C4	0.057 (2)	0.076 (2)	0.057 (2)	0.0128 (19)	0.0042 (18)	−0.0003 (19)

S—C1	1.700 (4)	C2—C3	1.333 (5)
S—C2	1.712 (3)	C2—C4	1.482 (5)
N—C1	1.275 (5)	C3—H3A	0.9300
N—C3	1.367 (5)	C4—H4A	0.9700
Cl1—C1	1.705 (3)	C4—H4B	0.9700
Cl2—C4	1.772 (4)
C1—S—C2	89.16 (17)	C2—C3—H3A	121.3
C1—N—C3	108.9 (3)	N—C3—H3A	121.3
N—C1—S	116.2 (3)	C2—C4—Cl2	112.0 (3)
N—C1—Cl1	122.9 (3)	C2—C4—H4A	109.2
S—C1—Cl1	120.9 (2)	Cl2—C4—H4A	109.2
C3—C2—C4	129.4 (3)	C2—C4—H4B	109.2
C3—C2—S	108.3 (3)	Cl2—C4—H4B	109.2
C4—C2—S	122.3 (3)	H4A—C4—H4B	107.9
C2—C3—N	117.5 (3)
C3—N—C1—S	0.0 (5)	C4—C2—C3—N	177.2 (4)
C3—N—C1—Cl1	179.6 (3)	S—C2—C3—N	0.0 (5)
C2—S—C1—N	0.0 (4)	C1—N—C3—C2	0.0 (6)
C2—S—C1—Cl1	−179.6 (2)	C3—C2—C4—Cl2	116.5 (4)
C1—S—C2—C3	0.0 (3)	S—C2—C4—Cl2	−66.6 (4)
C1—S—C2—C4	−177.4 (3)