N-(3,4-Dichloro-phen-yl)thio-urea.

In the title compound, C(7)H(6)Cl(2)N(2)S, the benzene ring and the mean plane of the thio-urea fragment [-N-C(=S)-N] make a dihedral angle of 66.77 (3)°. Inter-molecular N-H⋯S and N-H⋯Cl hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Liu et al. (1994 ▶). For details of the biological activity of thia­zole and its derivatives, see: Holla et al. (2003 ▶).

Experimental

Crystal data

C7H6Cl2N2S

M = 221.10

Triclinic,

a = 5.8168 (19) Å

b = 8.489 (3) Å

c = 9.771 (3) Å

α = 107.042 (4)°

β = 94.468 (4)°

γ = 94.778 (4)°

V = 457.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.88 mm−1

T = 291 K

0.15 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.879, T max = 0.933

1882 measured reflections

1562 independent reflections

1410 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.236

S = 1.10

1562 reflections

122 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.76 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809035569/bg2297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035569/bg2297Isup2.hkl

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

C7H6Cl2N2S	Z = 2
Mr = 221.10	F(000) = 224
Triclinic, P1	Dx = 1.607 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8168 (19) Å	Cell parameters from 843 reflections
b = 8.489 (3) Å	θ = 2.5–27.0°
c = 9.771 (3) Å	µ = 0.88 mm−1
α = 107.042 (4)°	T = 291 K
β = 94.468 (4)°	Prism, orange
γ = 94.778 (4)°	0.15 × 0.10 × 0.08 mm
V = 457.0 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	1562 independent reflections
Radiation source: fine-focus sealed tube	1410 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→3
Tmin = 0.879, Tmax = 0.933	k = −9→10
1882 measured reflections	l = −11→11

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)] = 0.084	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.236	w = 1/[σ2(Fo2) + (0.1955P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1562 reflections	Δρmax = 0.75 e Å−3
122 parameters	Δρmin = −0.76 e Å−3
3 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: 0.13 (4)

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	0.19736 (17)	0.43998 (14)	0.66939 (11)	0.0560 (6)
Cl2	−0.27770 (17)	0.21189 (14)	0.62155 (11)	0.0565 (6)
C1	0.1662 (6)	0.1685 (4)	0.2584 (4)	0.0365 (9)
C2	0.2383 (6)	0.2836 (4)	0.3921 (4)	0.0398 (9)
H2	0.3777	0.3512	0.4062	0.048*
C3	0.1023 (6)	0.2971 (4)	0.5034 (4)	0.0374 (9)
C4	−0.1046 (6)	0.1948 (4)	0.4830 (4)	0.0388 (9)
C5	−0.1748 (6)	0.0795 (5)	0.3507 (4)	0.0480 (11)
H5	−0.3127	0.0103	0.3372	0.058*
C6	−0.0398 (7)	0.0669 (4)	0.2380 (4)	0.0446 (9)
H6	−0.0879	−0.0101	0.1485	0.054*
N7	0.3073 (6)	0.1521 (3)	0.1444 (3)	0.0424 (9)
H7X	0.371 (7)	0.061 (4)	0.113 (5)	0.071 (15)*
C8	0.3732 (6)	0.2709 (4)	0.0853 (4)	0.0353 (8)
S9	0.58001 (18)	0.24215 (10)	−0.03037 (11)	0.0493 (6)
N10	0.2718 (6)	0.4075 (4)	0.1191 (4)	0.0508 (10)
H10X	0.308 (7)	0.486 (5)	0.083 (5)	0.055 (12)*
H10Y	0.159 (5)	0.422 (6)	0.173 (4)	0.054 (12)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0546 (8)	0.0620 (8)	0.0427 (7)	0.0057 (5)	0.0146 (5)	0.0001 (5)
Cl2	0.0577 (8)	0.0636 (9)	0.0549 (8)	0.0087 (5)	0.0328 (5)	0.0209 (6)
C1	0.0534 (19)	0.0253 (16)	0.0377 (19)	0.0123 (14)	0.0214 (15)	0.0137 (14)
C2	0.0404 (18)	0.0334 (18)	0.050 (2)	0.0026 (14)	0.0167 (15)	0.0160 (16)
C3	0.0453 (19)	0.0341 (18)	0.0375 (19)	0.0122 (14)	0.0132 (14)	0.0139 (15)
C4	0.0433 (19)	0.0396 (19)	0.042 (2)	0.0106 (15)	0.0200 (15)	0.0195 (16)
C5	0.048 (2)	0.043 (2)	0.051 (2)	−0.0046 (16)	0.0107 (18)	0.0127 (18)
C6	0.060 (2)	0.0344 (19)	0.039 (2)	0.0023 (15)	0.0123 (16)	0.0087 (15)
N7	0.064 (2)	0.0251 (15)	0.0460 (18)	0.0146 (13)	0.0319 (14)	0.0136 (13)
C8	0.0489 (19)	0.0257 (16)	0.0338 (18)	0.0059 (13)	0.0167 (14)	0.0091 (13)
S9	0.0722 (9)	0.0288 (7)	0.0572 (8)	0.0151 (5)	0.0417 (6)	0.0175 (5)
N10	0.072 (2)	0.0312 (17)	0.064 (2)	0.0175 (15)	0.0434 (17)	0.0239 (15)

Cl1—C3	1.733 (4)	C5—C6	1.386 (5)
Cl2—C4	1.729 (4)	C5—H5	0.9300
C1—C6	1.382 (5)	C6—H6	0.9300
C1—C2	1.391 (5)	N7—C8	1.345 (4)
C1—N7	1.416 (5)	N7—H7X	0.87 (2)
C2—C3	1.378 (6)	C8—N10	1.312 (5)
C2—H2	0.9300	C8—S9	1.698 (4)
C3—C4	1.389 (5)	N10—H10X	0.86 (3)
C4—C5	1.380 (6)	N10—H10Y	0.87 (3)
C6—C1—C2	120.1 (3)	C6—C5—H5	120.0
C6—C1—N7	120.0 (3)	C1—C6—C5	120.0 (3)
C2—C1—N7	120.0 (3)	C1—C6—H6	120.0
C3—C2—C1	119.7 (3)	C5—C6—H6	120.0
C3—C2—H2	120.1	C8—N7—C1	126.3 (3)
C1—C2—H2	120.1	C8—N7—H7X	114 (3)
C2—C3—C4	120.2 (3)	C1—N7—H7X	119 (3)
C2—C3—Cl1	118.9 (3)	N10—C8—N7	118.0 (3)
C4—C3—Cl1	120.9 (3)	N10—C8—S9	121.7 (3)
C5—C4—C3	119.9 (3)	N7—C8—S9	120.4 (3)
C5—C4—Cl2	119.5 (3)	C8—N10—H10X	121 (3)
C3—C4—Cl2	120.6 (3)	C8—N10—H10Y	123 (3)
C4—C5—C6	120.0 (3)	H10X—N10—H10Y	116 (4)
C4—C5—H5	120.0
C6—C1—C2—C3	−0.7 (5)	Cl2—C4—C5—C6	178.7 (3)
N7—C1—C2—C3	−178.9 (3)	C2—C1—C6—C5	0.0 (5)
C1—C2—C3—C4	0.9 (5)	N7—C1—C6—C5	178.1 (3)
C1—C2—C3—Cl1	179.3 (3)	C4—C5—C6—C1	0.6 (5)
C2—C3—C4—C5	−0.2 (5)	C6—C1—N7—C8	121.2 (4)
Cl1—C3—C4—C5	−178.7 (3)	C2—C1—N7—C8	−60.7 (5)
C2—C3—C4—Cl2	−179.5 (2)	C1—N7—C8—N10	−11.2 (5)
Cl1—C3—C4—Cl2	2.1 (4)	C1—N7—C8—S9	169.3 (3)
C3—C4—C5—C6	−0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7X···S9i	0.86 (3)	2.51 (2)	3.342 (3)	161 (4)
N10—H10Y···Cl1ii	0.87 (3)	2.80 (2)	3.646 (3)	163 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7X⋯S9i	0.86 (3)	2.51 (2)	3.342 (3)	161 (4)
N10—H10Y⋯Cl1ii	0.87 (3)	2.80 (2)	3.646 (3)	163 (4)

Symmetry codes: (i) ; (ii) .