2-(2,4-Di-chloro-phen-yl)-N-(1,3-thia-zol-2-yl)acetamide.

In the title compound, C11H8Cl2N2OS, the mean plane of the di-chloro-phenyl ring is twisted by 72.4 (1)° from that of the thia-zole ring. In the crystal, mol-ecules are linked via pairs of N-H⋯N hydrogen bonds with an R 2 (2)(8) graph-set motif and weak C-H⋯O inter-actions, forming inversion dimers which stack along the c-axis direction.

Related literature

For the structural similarity of N-substituted 2-aryl­acetamides to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Fun et al. (2012a ▶,b ▶,c ▶,d ▶,e ▶); Butcher et al. (2013a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H8Cl2N2OS

M = 287.15

Triclinic,

a = 5.3262 (2) Å

b = 10.5083 (4) Å

c = 10.8096 (4) Å

α = 83.900 (3)°

β = 86.301 (3)°

γ = 87.279 (4)°

V = 599.83 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.70 mm−1

T = 123 K

0.35 × 0.25 × 0.12 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.873, T max = 1.000

10769 measured reflections

6006 independent reflections

4329 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.112

S = 1.07

6006 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008532/hg5302sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008532/hg5302Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008532/hg5302Isup3.cml

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

C11H8Cl2N2OS	Z = 2
Mr = 287.15	F(000) = 292
Triclinic, P1	Dx = 1.590 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3262 (2) Å	Cell parameters from 4451 reflections
b = 10.5083 (4) Å	θ = 3.8–37.4°
c = 10.8096 (4) Å	µ = 0.70 mm−1
α = 83.900 (3)°	T = 123 K
β = 86.301 (3)°	Prism, colorless
γ = 87.279 (4)°	0.35 × 0.25 × 0.12 mm
V = 599.83 (4) Å3

Agilent Xcalibur (Ruby, Gemini) diffractometer	6006 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4329 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10.5081 pixels mm-1	θmax = 37.5°, θmin = 3.8°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −17→17
Tmin = 0.873, Tmax = 1.000	l = −18→11
10769 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0402P)2] where P = (Fo2 + 2Fc2)/3
6006 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.79895 (7)	0.48741 (3)	0.89686 (3)	0.02461 (8)
Cl2	0.55890 (9)	0.83944 (4)	0.52220 (4)	0.03766 (11)
S1	1.04354 (7)	0.01947 (3)	0.74851 (3)	0.02147 (8)
O1	0.79783 (18)	0.25361 (10)	0.71093 (9)	0.0215 (2)
N1	0.6082 (2)	0.11595 (11)	0.86027 (10)	0.0186 (2)
H1A	0.4759	0.1039	0.9126	0.022*
N2	0.7798 (2)	−0.08345 (11)	0.93865 (10)	0.0192 (2)
C1	0.4325 (2)	0.45348 (12)	0.74111 (11)	0.0171 (2)
C2	0.6152 (2)	0.53376 (12)	0.77059 (11)	0.0174 (2)
C3	0.6586 (3)	0.65234 (13)	0.70372 (12)	0.0206 (3)
H3A	0.7876	0.7045	0.7242	0.025*
C4	0.5064 (3)	0.69139 (13)	0.60622 (12)	0.0217 (3)
C5	0.3151 (3)	0.61785 (14)	0.57565 (12)	0.0222 (3)
H5A	0.2096	0.6478	0.5102	0.027*
C6	0.2813 (3)	0.49878 (13)	0.64318 (12)	0.0199 (2)
H6A	0.1522	0.4469	0.6223	0.024*
C7	0.3992 (2)	0.32251 (13)	0.80963 (12)	0.0191 (2)
H7A	0.2454	0.2866	0.7829	0.023*
H7B	0.3745	0.3306	0.9001	0.023*
C8	0.6212 (2)	0.23051 (12)	0.78742 (11)	0.0166 (2)
C9	0.7900 (2)	0.01826 (12)	0.85656 (11)	0.0170 (2)
C10	1.1457 (3)	−0.12670 (14)	0.81987 (13)	0.0237 (3)
H10A	1.2938	−0.1734	0.7945	0.028*
C11	0.9844 (3)	−0.16548 (13)	0.91734 (13)	0.0216 (3)
H11A	1.0106	−0.2441	0.9678	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.02368 (17)	0.02474 (17)	0.02565 (16)	0.00123 (13)	−0.00852 (12)	−0.00047 (12)
Cl2	0.0557 (3)	0.02104 (18)	0.03370 (19)	−0.00763 (18)	−0.00098 (18)	0.01074 (15)
S1	0.02054 (16)	0.02107 (16)	0.02141 (15)	0.00019 (13)	0.00441 (12)	0.00039 (12)
O1	0.0212 (5)	0.0200 (5)	0.0211 (4)	0.0003 (4)	0.0032 (4)	0.0045 (4)
N1	0.0157 (5)	0.0160 (5)	0.0220 (5)	0.0006 (4)	0.0036 (4)	0.0045 (4)
N2	0.0183 (5)	0.0156 (5)	0.0224 (5)	0.0004 (4)	0.0010 (4)	0.0023 (4)
C1	0.0153 (5)	0.0155 (5)	0.0193 (5)	0.0004 (4)	0.0007 (4)	0.0018 (4)
C2	0.0164 (5)	0.0166 (5)	0.0189 (5)	0.0014 (4)	−0.0016 (4)	−0.0002 (4)
C3	0.0206 (6)	0.0169 (6)	0.0238 (6)	−0.0017 (5)	0.0011 (5)	−0.0008 (5)
C4	0.0277 (7)	0.0154 (6)	0.0201 (5)	0.0007 (5)	0.0041 (5)	0.0024 (4)
C5	0.0255 (7)	0.0208 (6)	0.0191 (5)	0.0030 (5)	−0.0022 (5)	0.0023 (5)
C6	0.0180 (6)	0.0197 (6)	0.0218 (5)	−0.0002 (5)	−0.0026 (4)	0.0002 (5)
C7	0.0169 (6)	0.0158 (5)	0.0231 (6)	−0.0005 (5)	0.0009 (4)	0.0036 (4)
C8	0.0178 (6)	0.0148 (5)	0.0170 (5)	−0.0013 (4)	−0.0026 (4)	0.0012 (4)
C9	0.0155 (5)	0.0165 (5)	0.0185 (5)	−0.0015 (4)	0.0003 (4)	0.0002 (4)
C10	0.0206 (6)	0.0205 (6)	0.0291 (6)	0.0041 (5)	0.0020 (5)	−0.0027 (5)
C11	0.0218 (6)	0.0166 (6)	0.0256 (6)	0.0008 (5)	−0.0007 (5)	0.0002 (5)

Cl1—C2	1.7445 (12)	C2—C3	1.3939 (17)
Cl2—C4	1.7412 (13)	C3—C4	1.3866 (19)
S1—C10	1.7243 (14)	C3—H3A	0.9500
S1—C9	1.7272 (13)	C4—C5	1.384 (2)
O1—C8	1.2274 (15)	C5—C6	1.3933 (18)
N1—C8	1.3687 (15)	C5—H5A	0.9500
N1—C9	1.3794 (17)	C6—H6A	0.9500
N1—H1A	0.8800	C7—C8	1.5148 (19)
N2—C9	1.3155 (15)	C7—H7A	0.9900
N2—C11	1.3799 (18)	C7—H7B	0.9900
C1—C2	1.3912 (19)	C10—C11	1.3563 (19)
C1—C6	1.4009 (17)	C10—H10A	0.9500
C1—C7	1.5046 (17)	C11—H11A	0.9500
C10—S1—C9	88.73 (6)	C5—C6—H6A	119.1
C8—N1—C9	123.92 (11)	C1—C6—H6A	119.1
C8—N1—H1A	118.0	C1—C7—C8	113.05 (10)
C9—N1—H1A	118.0	C1—C7—H7A	109.0
C9—N2—C11	109.73 (11)	C8—C7—H7A	109.0
C2—C1—C6	117.23 (11)	C1—C7—H7B	109.0
C2—C1—C7	121.89 (11)	C8—C7—H7B	109.0
C6—C1—C7	120.88 (12)	H7A—C7—H7B	107.8
C1—C2—C3	122.75 (12)	O1—C8—N1	121.81 (12)
C1—C2—Cl1	119.76 (9)	O1—C8—C7	124.30 (11)
C3—C2—Cl1	117.49 (10)	N1—C8—C7	113.88 (10)
C4—C3—C2	117.54 (13)	N2—C9—N1	120.68 (11)
C4—C3—H3A	121.2	N2—C9—S1	115.46 (10)
C2—C3—H3A	121.2	N1—C9—S1	123.86 (9)
C5—C4—C3	122.29 (12)	C11—C10—S1	110.33 (11)
C5—C4—Cl2	119.82 (10)	C11—C10—H10A	124.8
C3—C4—Cl2	117.89 (11)	S1—C10—H10A	124.8
C4—C5—C6	118.37 (12)	C10—C11—N2	115.75 (12)
C4—C5—H5A	120.8	C10—C11—H11A	122.1
C6—C5—H5A	120.8	N2—C11—H11A	122.1
C5—C6—C1	121.75 (13)
C6—C1—C2—C3	−2.9 (2)	C6—C1—C7—C8	112.46 (14)
C7—C1—C2—C3	176.27 (13)	C9—N1—C8—O1	1.1 (2)
C6—C1—C2—Cl1	176.52 (10)	C9—N1—C8—C7	−179.52 (12)
C7—C1—C2—Cl1	−4.33 (19)	C1—C7—C8—O1	−8.1 (2)
C1—C2—C3—C4	1.7 (2)	C1—C7—C8—N1	172.59 (11)
Cl1—C2—C3—C4	−177.67 (11)	C11—N2—C9—N1	−178.62 (12)
C2—C3—C4—C5	0.9 (2)	C11—N2—C9—S1	0.80 (15)
C2—C3—C4—Cl2	179.95 (11)	C8—N1—C9—N2	172.32 (12)
C3—C4—C5—C6	−2.1 (2)	C8—N1—C9—S1	−7.0 (2)
Cl2—C4—C5—C6	178.79 (11)	C10—S1—C9—N2	−0.69 (11)
C4—C5—C6—C1	0.9 (2)	C10—S1—C9—N1	178.71 (13)
C2—C1—C6—C5	1.5 (2)	C9—S1—C10—C11	0.35 (12)
C7—C1—C6—C5	−177.65 (13)	S1—C10—C11—N2	0.02 (18)
C2—C1—C7—C8	−66.66 (17)	C9—N2—C11—C10	−0.52 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1i	0.95	2.50	3.3253 (15)	145
N1—H1A···N2ii	0.88	2.04	2.9052 (15)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1i	0.95	2.50	3.3253 (15)	145
N1—H1A⋯N2ii	0.88	2.04	2.9052 (15)	168

Symmetry codes: (i) ; (ii) .