N-(2,4-Dichloro-phen-yl)-1,3-thia-zol-2-amine.

In the title mol-ecule, C(9)H(6)Cl(2)N(2)S, the mean planes of the benzene and thia-zole rings make a dihedral angle of 54.18 (8)°. In the crystal, mol-ecules are joined into dimers with an R(2) (2)(8) ring motif by pairs of N-H⋯N hydrogen bonds. These dimers are linked by C-H⋯Cl inter-actions into layers parallel to (011). The thia-zole rings form columns along the c-axis direction, with a centroid-centroid separation of 3.8581 (9) Å, indicating π-π inter-actions. An intra-molecular C-H⋯S contact also occurs.

Related literature

For the synthesis and crystal structure of a related compound, see: Babar et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H6Cl2N2S

M = 245.12

Monoclinic,

a = 13.0270 (9) Å

b = 10.1183 (6) Å

c = 7.7159 (5) Å

β = 91.974 (3)°

V = 1016.44 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.80 mm−1

T = 296 K

0.33 × 0.28 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.778, T max = 0.844

8039 measured reflections

2245 independent reflections

1957 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.04

2245 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035301/yk2069sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035301/yk2069Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035301/yk2069Isup3.cml

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

C9H6Cl2N2S	F(000) = 496
Mr = 245.12	Dx = 1.602 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 912 reflections
a = 13.0270 (9) Å	θ = 1.6–27.2°
b = 10.1183 (6) Å	µ = 0.80 mm−1
c = 7.7159 (5) Å	T = 296 K
β = 91.974 (3)°	Prism, yellow
V = 1016.44 (11) Å3	0.33 × 0.28 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	2245 independent reflections
Radiation source: fine-focus sealed tube	1957 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 7.80 pixels mm-1	θmax = 27.2°, θmin = 1.6°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.778, Tmax = 0.844	l = −9→9
8039 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.2925P] where P = (Fo2 + 2Fc2)/3
2245 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.24571 (4)	0.37457 (5)	0.29544 (6)	0.0545 (2)
Cl2	−0.05984 (3)	0.34681 (6)	0.74042 (8)	0.0662 (2)
S1	0.33053 (3)	0.77775 (4)	0.66934 (5)	0.0405 (1)
N1	0.35990 (10)	0.51946 (12)	0.57795 (18)	0.0403 (4)
N2	0.49723 (10)	0.66580 (13)	0.57830 (18)	0.0400 (4)
C1	0.26014 (11)	0.48156 (14)	0.6171 (2)	0.0353 (4)
C2	0.19932 (12)	0.41107 (15)	0.4977 (2)	0.0369 (4)
C3	0.10147 (12)	0.36979 (16)	0.5348 (2)	0.0434 (5)
C4	0.06296 (12)	0.40070 (17)	0.6935 (2)	0.0451 (5)
C5	0.12029 (14)	0.47052 (18)	0.8147 (2)	0.0505 (6)
C6	0.21843 (14)	0.50928 (18)	0.7763 (2)	0.0463 (5)
C7	0.40145 (11)	0.64084 (14)	0.60680 (18)	0.0326 (4)
C8	0.43848 (14)	0.87355 (15)	0.6496 (2)	0.0455 (5)
C9	0.51714 (14)	0.79861 (16)	0.6017 (2)	0.0462 (5)
H1	0.39818	0.46092	0.53165	0.0483*
H3	0.06225	0.32185	0.45384	0.0520*
H5	0.09331	0.49142	0.92130	0.0606*
H6	0.25772	0.55521	0.85926	0.0556*
H8	0.44170	0.96415	0.66933	0.0545*
H9	0.58188	0.83417	0.58503	0.0554*

	U11	U22	U33	U12	U13	U23
Cl1	0.0514 (3)	0.0636 (3)	0.0487 (3)	−0.0090 (2)	0.0058 (2)	−0.0158 (2)
Cl2	0.0351 (2)	0.0737 (3)	0.0905 (4)	−0.0031 (2)	0.0114 (2)	0.0243 (3)
S1	0.0421 (2)	0.0346 (2)	0.0453 (2)	0.0064 (2)	0.0081 (2)	−0.0047 (2)
N1	0.0325 (7)	0.0334 (6)	0.0554 (8)	−0.0019 (5)	0.0082 (6)	−0.0134 (6)
N2	0.0350 (7)	0.0333 (6)	0.0519 (8)	−0.0022 (5)	0.0059 (6)	−0.0070 (6)
C1	0.0319 (7)	0.0302 (7)	0.0438 (8)	0.0008 (6)	0.0034 (6)	−0.0011 (6)
C2	0.0365 (8)	0.0338 (7)	0.0405 (8)	0.0009 (6)	0.0019 (6)	−0.0005 (6)
C3	0.0351 (8)	0.0396 (8)	0.0550 (10)	−0.0030 (6)	−0.0047 (7)	0.0039 (7)
C4	0.0319 (8)	0.0420 (9)	0.0619 (11)	0.0019 (7)	0.0075 (7)	0.0141 (8)
C5	0.0470 (10)	0.0526 (10)	0.0530 (10)	0.0006 (8)	0.0170 (8)	−0.0013 (8)
C6	0.0454 (9)	0.0480 (9)	0.0458 (9)	−0.0049 (7)	0.0059 (7)	−0.0078 (7)
C7	0.0342 (8)	0.0313 (7)	0.0325 (7)	0.0025 (6)	0.0021 (6)	−0.0045 (5)
C8	0.0567 (10)	0.0289 (7)	0.0511 (9)	−0.0023 (7)	0.0071 (8)	−0.0040 (7)
C9	0.0449 (9)	0.0357 (8)	0.0583 (10)	−0.0084 (7)	0.0080 (8)	−0.0052 (7)

Cl1—C2	1.7327 (16)	C2—C3	1.381 (2)
Cl2—C4	1.7399 (16)	C3—C4	1.375 (2)
S1—C7	1.7425 (15)	C4—C5	1.372 (2)
S1—C8	1.7191 (18)	C5—C6	1.379 (3)
N1—C1	1.3979 (19)	C8—C9	1.337 (2)
N1—C7	1.3574 (19)	C3—H3	0.9300
N2—C7	1.2992 (19)	C5—H5	0.9300
N2—C9	1.379 (2)	C6—H6	0.9300
N1—H1	0.8600	C8—H8	0.9300
C1—C6	1.389 (2)	C9—H9	0.9300
C1—C2	1.391 (2)
C7—S1—C8	88.89 (7)	C1—C6—C5	121.76 (15)
C1—N1—C7	125.53 (13)	S1—C7—N2	114.44 (11)
C7—N2—C9	110.16 (13)	S1—C7—N1	123.54 (11)
C7—N1—H1	117.00	N1—C7—N2	121.87 (13)
C1—N1—H1	117.00	S1—C8—C9	109.99 (12)
N1—C1—C6	122.05 (14)	N2—C9—C8	116.50 (16)
N1—C1—C2	120.67 (14)	C2—C3—H3	121.00
C2—C1—C6	117.26 (14)	C4—C3—H3	121.00
C1—C2—C3	121.78 (14)	C4—C5—H5	120.00
Cl1—C2—C3	118.39 (12)	C6—C5—H5	120.00
Cl1—C2—C1	119.83 (12)	C1—C6—H6	119.00
C2—C3—C4	118.92 (15)	C5—C6—H6	119.00
C3—C4—C5	121.14 (15)	S1—C8—H8	125.00
Cl2—C4—C3	118.70 (12)	C9—C8—H8	125.00
Cl2—C4—C5	120.15 (13)	N2—C9—H9	122.00
C4—C5—C6	119.13 (15)	C8—C9—H9	122.00
C8—S1—C7—N1	−174.25 (13)	C6—C1—C2—Cl1	179.25 (12)
C8—S1—C7—N2	1.39 (12)	C6—C1—C2—C3	−0.1 (2)
C7—S1—C8—C9	−0.80 (12)	N1—C1—C6—C5	−179.38 (15)
C7—N1—C1—C2	134.53 (16)	C2—C1—C6—C5	−0.9 (2)
C7—N1—C1—C6	−47.0 (2)	Cl1—C2—C3—C4	−178.59 (13)
C1—N1—C7—S1	−9.7 (2)	C1—C2—C3—C4	0.8 (2)
C1—N1—C7—N2	174.96 (14)	C2—C3—C4—Cl2	−179.29 (12)
C9—N2—C7—S1	−1.53 (17)	C2—C3—C4—C5	−0.5 (3)
C9—N2—C7—N1	174.19 (14)	Cl2—C4—C5—C6	178.34 (14)
C7—N2—C9—C8	0.9 (2)	C3—C4—C5—C6	−0.5 (3)
N1—C1—C2—Cl1	−2.2 (2)	C4—C5—C6—C1	1.2 (3)
N1—C1—C2—C3	178.44 (14)	S1—C8—C9—N2	0.13 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.07	2.9302 (19)	174
C3—H3···Cl2ii	0.93	2.82	3.7483 (17)	173
C6—H6···S1	0.93	2.87	3.2056 (19)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.86	2.07	2.9302 (19)	174
C3—H3⋯Cl2ii	0.93	2.82	3.7483 (17)	173
C6—H6⋯S1	0.93	2.87	3.2056 (19)	103

Symmetry codes: (i) ; (ii) .