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

In the mol-ecular structure of the title compound, C(10)H(6)Cl(2)N(2)OS, the dihedral angle between the benzene plane and the plane defined by the amide functionality is 8.6 (1)°, while the thia-zole ring plane is twisted with respect to the amide plane by 68.71 (5)°. In the crystal, pairs of inter-molecular N-H⋯N hydrogen-bond inter-actions connect the mol-ecules into inversion dimers. π-π inter-actions are also observed between neighbouring thia-zole and phen-yl rings [centroid-centroid distance = 3.5905 (13) Å] and a weak C-H⋯π interaction also occurs.

Related literature

For the synthesis of related thia­zole derivatives and their application, see: Raman et al. (2000 ▶); Yunus et al. (2007 ▶, 2008 ▶). For microwave-assisted synthesis of amides, see Wang et al. (2008 ▶).

Experimental

Crystal data

C10H6Cl2N2OS

M = 273.13

Monoclinic,

a = 14.054 (3) Å

b = 13.063 (3) Å

c = 6.2880 (14) Å

β = 101.578 (3)°

V = 1130.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 304 K

0.38 × 0.27 × 0.07 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.768, T max = 0.950

5906 measured reflections

1993 independent reflections

1820 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.06

1993 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT and CrystalStructure (Rigaku/MSC, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELX97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044193/im2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044193/im2236Isup2.hkl

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

C10H6Cl2N2OS	F(000) = 552
Mr = 273.13	Dx = 1.604 Mg m−3
Monoclinic, P21/c	Melting point: 487 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.054 (3) Å	Cell parameters from 6065 reflections
b = 13.063 (3) Å	θ = 2.2–25.0°
c = 6.2880 (14) Å	µ = 0.74 mm−1
β = 101.578 (3)°	T = 304 K
V = 1130.8 (4) Å3	Block, colourless
Z = 4	0.38 × 0.27 × 0.07 mm

Bruker SMART 1000 CCD diffractometer	1993 independent reflections
Radiation source: fine-focus sealed tube	1820 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
Tmin = 0.768, Tmax = 0.950	k = −15→13
5906 measured reflections	l = −6→7

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 atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.4293P] where P = (Fo2 + 2Fc2)/3
1993 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.24 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	0.24941 (4)	0.64173 (4)	0.24448 (11)	0.0739 (2)
Cl2	0.02120 (5)	0.61769 (6)	0.82771 (11)	0.0849 (2)
S1	0.41434 (3)	0.32850 (4)	0.00755 (7)	0.04892 (15)
O1	0.25039 (10)	0.34891 (11)	0.1798 (2)	0.0592 (4)
N1	0.53725 (10)	0.42950 (11)	0.2878 (2)	0.0452 (3)
N2	0.38052 (10)	0.43647 (12)	0.3593 (3)	0.0441 (3)
C1	0.53294 (15)	0.33469 (15)	−0.0224 (3)	0.0536 (5)
H1	0.5568	0.3037	−0.1343	0.064*
C2	0.58651 (14)	0.39011 (15)	0.1371 (3)	0.0500 (4)
H2	0.6525	0.4013	0.1457	0.060*
C3	0.44612 (12)	0.40332 (12)	0.2379 (3)	0.0399 (4)
C4	0.28500 (12)	0.41126 (13)	0.3182 (3)	0.0436 (4)
C5	0.22451 (12)	0.46497 (13)	0.4549 (3)	0.0435 (4)
C6	0.20114 (12)	0.56805 (14)	0.4270 (3)	0.0471 (4)
C7	0.13838 (13)	0.61528 (15)	0.5405 (3)	0.0549 (5)
H7	0.1220	0.6839	0.5175	0.066*
C8	0.10102 (13)	0.55811 (18)	0.6880 (3)	0.0571 (5)
C9	0.12440 (15)	0.45612 (18)	0.7240 (4)	0.0637 (5)
H9	0.0997	0.4191	0.8271	0.076*
C10	0.18494 (14)	0.40987 (16)	0.6047 (3)	0.0561 (5)
H10	0.1994	0.3407	0.6252	0.067*
H2N	0.4017 (14)	0.4739 (16)	0.456 (3)	0.048 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0751 (4)	0.0560 (3)	0.1005 (5)	0.0071 (3)	0.0411 (3)	0.0226 (3)
Cl2	0.0658 (4)	0.1064 (5)	0.0910 (5)	0.0030 (3)	0.0361 (3)	−0.0242 (4)
S1	0.0525 (3)	0.0473 (3)	0.0460 (3)	−0.00460 (19)	0.0078 (2)	−0.01145 (19)
O1	0.0506 (8)	0.0593 (8)	0.0655 (9)	−0.0091 (6)	0.0061 (6)	−0.0187 (7)
N1	0.0420 (8)	0.0449 (8)	0.0487 (8)	−0.0020 (6)	0.0095 (6)	−0.0084 (6)
N2	0.0398 (8)	0.0430 (8)	0.0485 (8)	−0.0022 (6)	0.0064 (6)	−0.0130 (7)
C1	0.0596 (11)	0.0544 (11)	0.0499 (10)	−0.0013 (9)	0.0186 (9)	−0.0099 (8)
C2	0.0471 (10)	0.0517 (11)	0.0540 (10)	−0.0015 (8)	0.0168 (8)	−0.0067 (8)
C3	0.0446 (9)	0.0331 (8)	0.0411 (9)	0.0008 (7)	0.0065 (7)	−0.0029 (7)
C4	0.0424 (9)	0.0385 (9)	0.0479 (9)	−0.0003 (7)	0.0042 (7)	−0.0012 (7)
C5	0.0344 (8)	0.0457 (9)	0.0482 (9)	−0.0023 (7)	0.0035 (7)	−0.0020 (7)
C6	0.0399 (9)	0.0460 (10)	0.0555 (10)	−0.0028 (7)	0.0098 (8)	−0.0009 (8)
C7	0.0451 (10)	0.0489 (11)	0.0705 (13)	0.0011 (8)	0.0108 (9)	−0.0080 (9)
C8	0.0402 (9)	0.0740 (14)	0.0580 (11)	−0.0009 (9)	0.0123 (8)	−0.0108 (10)
C9	0.0597 (12)	0.0747 (15)	0.0614 (12)	−0.0019 (11)	0.0234 (10)	0.0083 (11)
C10	0.0534 (11)	0.0518 (11)	0.0635 (12)	0.0001 (9)	0.0123 (9)	0.0086 (9)

Cl1—C6	1.7370 (19)	C2—H2	0.9300
Cl2—C8	1.741 (2)	C4—C5	1.499 (2)
S1—C1	1.716 (2)	C5—C10	1.387 (3)
S1—C3	1.7299 (16)	C5—C6	1.389 (3)
O1—C4	1.219 (2)	C6—C7	1.386 (3)
N1—C3	1.302 (2)	C7—C8	1.374 (3)
N1—C2	1.381 (2)	C7—H7	0.9300
N2—C4	1.356 (2)	C8—C9	1.380 (3)
N2—C3	1.379 (2)	C9—C10	1.381 (3)
N2—H2N	0.79 (2)	C9—H9	0.9300
C1—C2	1.339 (3)	C10—H10	0.9300
C1—H1	0.9300
C1—S1—C3	88.40 (9)	C10—C5—C4	119.82 (16)
C3—N1—C2	109.94 (15)	C6—C5—C4	121.89 (16)
C4—N2—C3	124.36 (15)	C7—C6—C5	121.70 (17)
C4—N2—H2N	120.1 (14)	C7—C6—Cl1	117.84 (15)
C3—N2—H2N	115.5 (14)	C5—C6—Cl1	120.46 (14)
C2—C1—S1	110.84 (14)	C8—C7—C6	118.32 (19)
C2—C1—H1	124.6	C8—C7—H7	120.8
S1—C1—H1	124.6	C6—C7—H7	120.8
C1—C2—N1	115.56 (17)	C7—C8—C9	121.65 (19)
C1—C2—H2	122.2	C7—C8—Cl2	118.02 (17)
N1—C2—H2	122.2	C9—C8—Cl2	120.32 (17)
N1—C3—N2	121.23 (15)	C8—C9—C10	119.04 (19)
N1—C3—S1	115.25 (13)	C8—C9—H9	120.5
N2—C3—S1	123.49 (13)	C10—C9—H9	120.5
O1—C4—N2	122.43 (17)	C9—C10—C5	121.08 (19)
O1—C4—C5	122.07 (15)	C9—C10—H10	119.5
N2—C4—C5	115.51 (15)	C5—C10—H10	119.5
C10—C5—C6	118.16 (17)

Cg1 is the centroid of the thiazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N1i	0.79 (2)	2.09 (2)	2.880 (2)	178 (2)
C1—H1···Cg1ii	0.93	2.81	3.501 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the thia­zole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N1i	0.79 (2)	2.09 (2)	2.880 (2)	178 (2)
C1—H1⋯Cg1ii	0.93	2.81	3.501 (2)	132

Symmetry codes: (i) ; (ii) .