2-(2,6-Dichloro-phen-yl)-N-(1,3-thia-zol-2-yl)acetamide.

In the title compound, C11H8Cl2N2OS, the mean plane of the dichloro-phenyl ring is twisted by 79.7 (7)° from that of the thia-zole ring. In the crystal, molecules are linked via pairs of N-H⋯N hydrogen bonds, forming inversion dimers which stack along the a-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 = 7.1278 (4) Å

b = 8.4434 (4) Å

c = 10.3637 (6) Å

α = 95.341 (4)°

β = 106.140 (5)°

γ = 96.745 (4)°

V = 589.80 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.71 mm−1

T = 123 K

0.3 × 0.2 × 0.1 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ▶) T min = 0.909, T max = 1.000

10674 measured reflections

5881 independent reflections

4481 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.096

S = 1.05

5881 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.30 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/S1600536813006260/hg5297sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006260/hg5297Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006260/hg5297Isup3.cml

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

C11H8Cl2N2OS	Z = 2
Mr = 287.15	F(000) = 292
Triclinic, P1	Dx = 1.617 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1278 (4) Å	Cell parameters from 3814 reflections
b = 8.4434 (4) Å	θ = 3.1–37.5°
c = 10.3637 (6) Å	µ = 0.71 mm−1
α = 95.341 (4)°	T = 123 K
β = 106.140 (5)°	Prism, colorless
γ = 96.745 (4)°	0.3 × 0.2 × 0.1 mm
V = 589.80 (6) Å3

Agilent Xcalibur (Ruby, Gemini) diffractometer	5881 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 10.5081 pixels mm-1	θmax = 37.6°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	k = −13→14
Tmin = 0.909, Tmax = 1.000	l = −17→8
10674 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.0356P] where P = (Fo2 + 2Fc2)/3
5881 reflections	(Δ/σ)max = 0.001
159 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.30 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
S1	0.07341 (5)	0.70227 (3)	0.53736 (3)	0.01622 (7)
Cl1	0.33730 (6)	0.82751 (4)	0.07966 (4)	0.02553 (8)
Cl2	0.41255 (5)	0.22491 (3)	0.21194 (3)	0.02086 (7)
O1	0.23281 (15)	0.51841 (10)	0.38090 (10)	0.02131 (19)
N1	0.38161 (16)	0.77833 (11)	0.43229 (10)	0.01460 (18)
H1N	0.472 (3)	0.854 (2)	0.4214 (18)	0.033 (5)*
N2	0.30837 (16)	0.97170 (11)	0.58210 (10)	0.01568 (18)
C1	0.36862 (17)	0.52292 (13)	0.13841 (11)	0.01338 (19)
C2	0.29093 (19)	0.61876 (14)	0.03922 (13)	0.0166 (2)
C3	0.1754 (2)	0.55517 (16)	−0.09107 (13)	0.0203 (2)
H3A	0.1266	0.6242	−0.1559	0.024*
C4	0.1326 (2)	0.38945 (16)	−0.12497 (13)	0.0203 (2)
H4A	0.0532	0.3444	−0.2135	0.024*
C5	0.20517 (19)	0.28927 (14)	−0.03037 (13)	0.0183 (2)
H5A	0.1757	0.1757	−0.0536	0.022*
C6	0.32131 (18)	0.35632 (13)	0.09860 (12)	0.0146 (2)
C7	0.49054 (18)	0.59521 (14)	0.28024 (12)	0.0154 (2)
H7A	0.5705	0.6980	0.2768	0.019*
H7B	0.5820	0.5211	0.3199	0.019*
C8	0.35693 (18)	0.62512 (13)	0.36893 (12)	0.0147 (2)
C9	0.26992 (17)	0.82641 (13)	0.51500 (11)	0.01340 (19)
C10	0.1753 (2)	0.98851 (14)	0.65603 (13)	0.0184 (2)
H10A	0.1797	1.0856	0.7118	0.022*
C11	0.0385 (2)	0.85772 (14)	0.64385 (13)	0.0184 (2)
H11B	−0.0622	0.8526	0.6878	0.022*

	U11	U22	U33	U12	U13	U23
S1	0.01826 (14)	0.01396 (12)	0.01733 (13)	−0.00207 (9)	0.00928 (11)	−0.00039 (10)
Cl1	0.03479 (19)	0.01430 (12)	0.03140 (17)	0.00564 (11)	0.01460 (14)	0.00504 (11)
Cl2	0.02711 (16)	0.01518 (12)	0.02042 (14)	0.00524 (10)	0.00606 (12)	0.00315 (10)
O1	0.0265 (5)	0.0151 (4)	0.0240 (5)	−0.0047 (3)	0.0152 (4)	−0.0035 (3)
N1	0.0184 (5)	0.0107 (4)	0.0159 (4)	−0.0013 (3)	0.0095 (4)	−0.0019 (3)
N2	0.0189 (5)	0.0130 (4)	0.0161 (4)	0.0000 (3)	0.0088 (4)	−0.0014 (3)
C1	0.0147 (5)	0.0136 (4)	0.0131 (5)	0.0019 (4)	0.0070 (4)	−0.0008 (4)
C2	0.0195 (5)	0.0148 (5)	0.0193 (5)	0.0043 (4)	0.0108 (4)	0.0030 (4)
C3	0.0222 (6)	0.0264 (6)	0.0160 (5)	0.0085 (5)	0.0089 (5)	0.0054 (5)
C4	0.0175 (6)	0.0291 (6)	0.0136 (5)	0.0053 (5)	0.0045 (4)	−0.0025 (4)
C5	0.0182 (5)	0.0178 (5)	0.0176 (5)	0.0020 (4)	0.0055 (4)	−0.0044 (4)
C6	0.0157 (5)	0.0141 (4)	0.0145 (5)	0.0027 (4)	0.0058 (4)	−0.0002 (4)
C7	0.0160 (5)	0.0153 (5)	0.0148 (5)	−0.0007 (4)	0.0068 (4)	−0.0029 (4)
C8	0.0171 (5)	0.0136 (4)	0.0132 (5)	0.0005 (4)	0.0057 (4)	−0.0014 (4)
C9	0.0157 (5)	0.0124 (4)	0.0127 (4)	0.0008 (4)	0.0060 (4)	0.0007 (4)
C10	0.0230 (6)	0.0153 (5)	0.0196 (5)	0.0024 (4)	0.0117 (5)	−0.0009 (4)
C11	0.0200 (6)	0.0192 (5)	0.0190 (5)	0.0018 (4)	0.0119 (5)	0.0001 (4)

S1—C11	1.7212 (13)	C2—C3	1.3901 (18)
S1—C9	1.7306 (11)	C3—C4	1.3867 (19)
Cl1—C2	1.7436 (12)	C3—H3A	0.9500
Cl2—C6	1.7382 (12)	C4—C5	1.3854 (18)
O1—C8	1.2266 (14)	C4—H4A	0.9500
N1—C8	1.3637 (14)	C5—C6	1.3879 (17)
N1—C9	1.3870 (15)	C5—H5A	0.9500
N1—H1N	0.890 (19)	C7—C8	1.5217 (17)
N2—C9	1.3114 (14)	C7—H7A	0.9900
N2—C10	1.3863 (16)	C7—H7B	0.9900
C1—C2	1.4006 (16)	C10—C11	1.3562 (17)
C1—C6	1.4021 (15)	C10—H10A	0.9500
C1—C7	1.5121 (16)	C11—H11B	0.9500
C11—S1—C9	88.83 (6)	C5—C6—Cl2	117.37 (9)
C8—N1—C9	123.21 (10)	C1—C6—Cl2	119.94 (9)
C8—N1—H1N	120.7 (12)	C1—C7—C8	110.36 (10)
C9—N1—H1N	116.1 (12)	C1—C7—H7A	109.6
C9—N2—C10	109.52 (10)	C8—C7—H7A	109.6
C2—C1—C6	115.65 (11)	C1—C7—H7B	109.6
C2—C1—C7	121.89 (10)	C8—C7—H7B	109.6
C6—C1—C7	122.43 (10)	H7A—C7—H7B	108.1
C3—C2—C1	122.99 (11)	O1—C8—N1	122.19 (11)
C3—C2—Cl1	117.80 (9)	O1—C8—C7	121.94 (10)
C1—C2—Cl1	119.20 (9)	N1—C8—C7	115.86 (10)
C4—C3—C2	118.98 (11)	N2—C9—N1	121.19 (10)
C4—C3—H3A	120.5	N2—C9—S1	115.54 (9)
C2—C3—H3A	120.5	N1—C9—S1	123.27 (8)
C5—C4—C3	120.31 (12)	C11—C10—N2	115.85 (11)
C5—C4—H4A	119.8	C11—C10—H10A	122.1
C3—C4—H4A	119.8	N2—C10—H10A	122.1
C4—C5—C6	119.38 (11)	C10—C11—S1	110.26 (9)
C4—C5—H5A	120.3	C10—C11—H11B	124.9
C6—C5—H5A	120.3	S1—C11—H11B	124.9
C5—C6—C1	122.69 (11)
C6—C1—C2—C3	−0.48 (18)	C6—C1—C7—C8	−91.89 (13)
C7—C1—C2—C3	−178.78 (11)	C9—N1—C8—O1	0.06 (19)
C6—C1—C2—Cl1	178.78 (9)	C9—N1—C8—C7	179.00 (10)
C7—C1—C2—Cl1	0.48 (16)	C1—C7—C8—O1	53.64 (15)
C1—C2—C3—C4	0.69 (19)	C1—C7—C8—N1	−125.30 (11)
Cl1—C2—C3—C4	−178.58 (10)	C10—N2—C9—N1	179.79 (11)
C2—C3—C4—C5	−0.38 (19)	C10—N2—C9—S1	−0.23 (13)
C3—C4—C5—C6	−0.09 (19)	C8—N1—C9—N2	174.79 (11)
C4—C5—C6—C1	0.30 (19)	C8—N1—C9—S1	−5.18 (17)
C4—C5—C6—Cl2	−178.67 (10)	C11—S1—C9—N2	0.53 (10)
C2—C1—C6—C5	−0.02 (17)	C11—S1—C9—N1	−179.49 (10)
C7—C1—C6—C5	178.27 (11)	C9—N2—C10—C11	−0.31 (16)
C2—C1—C6—Cl2	178.92 (9)	N2—C10—C11—S1	0.70 (15)
C7—C1—C6—Cl2	−2.79 (16)	C9—S1—C11—C10	−0.66 (10)
C2—C1—C7—C8	86.29 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2i	0.890 (19)	2.030 (19)	2.9165 (14)	173.9 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2i	0.890 (19)	2.030 (19)	2.9165 (14)	173.9 (17)

Symmetry code: (i) .