2-(3,4-Dichloro­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

In the title compound, C₁₁H₈Cl₂N₂OS, the mean plane of the dichloro­phenyl ring is twisted by 61.8 (1)° from that of the thia­zole ring. In the crystal, mol­ecules are linked via pairs of N—H...N hydrogen bonds with an R₂²(8) graph-set motif, forming inversion dimers which stack along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.118
• Data-to-parameter ratio = 36.3

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.151
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     19.109
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      4.917
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.349
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          4
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         28

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          1
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        500

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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S1. Comment

N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2006, 2008). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008, 2010). Crystal structures of some acetamide derivatives viz., (2,2-diphenyl-N-(1,3-thiazol-2-yl)acetamide, 2-(4-chlorophenyl)-N-(1,3-thiazol-2-yl)acetamide, 2-(naphthalen-1-yl)-N-(1,3-thiazol-2-yl)acetamide, N-(1,3-thiazol-2-yl)-2-(2,4,6-trimethyl phenyl)acetamide, 2-(2-fluorophenyl)-N-(1,3-thiazol-2-yl)acetamide (Fun et al., 2012a,b,c,d,e), 2-(2,6-dichlorophenyl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yl)acetamide, 2-(2,4-Dichlorophenyl)-N-(1,5-dimethyl-3-oxo- 2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide (Butcher et al., 2013a,b) have been reported. In view of the importance of amides, we report herein the crystal structure of the title compound, C₁₁H₈Cl₂N₂OS, (I).

In (I), the mean plane of the dichlorophenyl ring is twisted by 61.8 (1)° from that of the thiazol ring (Fig. 1). Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, the molecules are linked via pairs of N—H···N hydrogen bonds in an R²₂(8) graph-set motif forming inversion dimers which stack along the a axis (Fig. 2).

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).

S2. Experimental

3,4-Dichlorophenylacetic acid (0.240 g, 1 mmol) and 2-aminothiazole (0.1 g, 1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) and were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring, which was extracted thrice with dichloromethane (Fig. 3). The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Single crystals were grown from methanol and acetone mixture (1:1) by the slow evaporation method (M.P.: 459–461K).

S3. Refinement

All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH), 0.99Å (CH₂) or 0.88Å (NH). Isotropic displacement parameters for these atoms were set to 1.18-1.22 (CH, CH₂) times U_eq of the parent atom.

Computing details

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the b axis. Dashed lines indicate N—H···N intermolecular hydrogen bonds in an R^22(8) graph-set motif forming inversion dimers which stack along the a axis. H atoms not involved in hydrogen bonding have been removed for clarity.
	Fig. 3. The preparation of the title compound.

2-(3,4-Dichlorophenyl)-N-(1,3-thiazol-2-yl)acetamide

Crystal data

C11H8Cl2N2OS	Z = 2
Mr = 287.15	F(000) = 292
Triclinic, P1	Dx = 1.646 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6185 (3) Å	Cell parameters from 4182 reflections
b = 7.7741 (7) Å	θ = 3.3–37.5°
c = 17.1188 (12) Å	µ = 0.72 mm^−1
α = 100.278 (7)°	T = 123 K
β = 94.250 (6)°	Prism, colorless
γ = 105.001 (7)°	0.55 × 0.19 × 0.12 mm
V = 579.47 (8) Å^3

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer	5597 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3860 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.151
Detector resolution: 10.5081 pixels mm^-1	θmax = 37.6°, θmin = 3.3°
ω scans	h = −7→7
Absorption correction: analytical (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −12→13
Tmin = 0.776, Tmax = 0.929	l = −25→28
9162 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0488P)^2] where P = (Fo^2 + 2Fc^2)/3
5597 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.81248 (12)	1.09847 (6)	0.14647 (3)	0.03477 (13)
Cl2	0.96349 (10)	0.77677 (6)	0.02962 (2)	0.02982 (11)
S1	0.76516 (8)	0.85914 (5)	0.54589 (2)	0.01625 (8)
O1	0.6604 (2)	0.80798 (16)	0.38585 (6)	0.0197 (2)
N1	0.2761 (3)	0.64533 (17)	0.44080 (7)	0.0139 (2)
H1A	0.0927	0.5703	0.4317	0.017*
N2	0.2939 (3)	0.63193 (17)	0.57692 (7)	0.0150 (2)
C1	0.3891 (3)	0.6615 (2)	0.22801 (8)	0.0152 (2)
C2	0.5038 (3)	0.8399 (2)	0.21780 (8)	0.0182 (3)
H2A	0.4619	0.9377	0.2526	0.022*
C3	0.6792 (3)	0.8744 (2)	0.15679 (8)	0.0193 (3)
C4	0.7428 (3)	0.7331 (2)	0.10493 (8)	0.0189 (3)
C5	0.6263 (4)	0.5551 (2)	0.11406 (9)	0.0204 (3)
H5A	0.6675	0.4575	0.0790	0.024*
C6	0.4486 (3)	0.5206 (2)	0.17508 (8)	0.0185 (3)
H6A	0.3667	0.3986	0.1805	0.022*
C7	0.2098 (3)	0.6289 (2)	0.29693 (8)	0.0172 (3)
H7A	0.1172	0.4966	0.2912	0.021*
H7B	0.0447	0.6883	0.2951	0.021*
C8	0.4065 (3)	0.70281 (19)	0.37754 (8)	0.0143 (2)
C9	0.4195 (3)	0.69989 (19)	0.51855 (8)	0.0129 (2)
C10	0.4805 (3)	0.7104 (2)	0.64816 (8)	0.0171 (3)
H10A	0.4282	0.6798	0.6976	0.020*
C11	0.7421 (3)	0.8335 (2)	0.64325 (8)	0.0181 (3)
H11B	0.8918	0.8969	0.6873	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0566 (3)	0.01772 (18)	0.0251 (2)	−0.00311 (18)	0.01475 (18)	0.00759 (15)
Cl2	0.0326 (2)	0.0360 (2)	0.01865 (17)	0.00221 (18)	0.01304 (15)	0.00638 (15)
S1	0.01359 (15)	0.01624 (16)	0.01658 (15)	−0.00031 (12)	0.00308 (11)	0.00343 (12)
O1	0.0146 (5)	0.0231 (5)	0.0182 (5)	−0.0024 (4)	0.0032 (4)	0.0067 (4)
N1	0.0127 (5)	0.0152 (5)	0.0132 (5)	0.0014 (4)	0.0032 (4)	0.0044 (4)
N2	0.0146 (5)	0.0162 (5)	0.0143 (5)	0.0024 (4)	0.0044 (4)	0.0048 (4)
C1	0.0147 (6)	0.0172 (6)	0.0129 (5)	0.0017 (5)	0.0015 (4)	0.0047 (5)
C2	0.0230 (7)	0.0170 (6)	0.0151 (6)	0.0047 (5)	0.0059 (5)	0.0044 (5)
C3	0.0245 (7)	0.0157 (6)	0.0146 (6)	−0.0014 (5)	0.0039 (5)	0.0047 (5)
C4	0.0198 (7)	0.0228 (7)	0.0121 (5)	0.0016 (5)	0.0038 (5)	0.0041 (5)
C5	0.0251 (7)	0.0205 (7)	0.0153 (6)	0.0067 (6)	0.0049 (5)	0.0017 (5)
C6	0.0218 (7)	0.0165 (6)	0.0159 (6)	0.0024 (5)	0.0027 (5)	0.0039 (5)
C7	0.0148 (6)	0.0210 (7)	0.0148 (6)	0.0016 (5)	0.0037 (4)	0.0055 (5)
C8	0.0143 (6)	0.0152 (6)	0.0138 (5)	0.0029 (5)	0.0044 (4)	0.0047 (4)
C9	0.0120 (5)	0.0125 (5)	0.0145 (5)	0.0030 (4)	0.0040 (4)	0.0032 (4)
C10	0.0190 (6)	0.0182 (6)	0.0140 (5)	0.0049 (5)	0.0030 (5)	0.0032 (5)
C11	0.0193 (7)	0.0190 (7)	0.0150 (6)	0.0049 (5)	0.0023 (5)	0.0018 (5)

Geometric parameters (Å, º)

Cl1—C3	1.7362 (15)	C2—C3	1.3897 (18)
Cl2—C4	1.7286 (13)	C2—H2A	0.9500
S1—C9	1.7203 (14)	C3—C4	1.392 (2)
S1—C11	1.7212 (14)	C4—C5	1.390 (2)
O1—C8	1.2251 (16)	C5—C6	1.397 (2)
N1—C8	1.3658 (15)	C5—H5A	0.9500
N1—C9	1.3829 (18)	C6—H6A	0.9500
N1—H1A	0.8800	C7—C8	1.523 (2)
N2—C9	1.3153 (16)	C7—H7A	0.9900
N2—C10	1.382 (2)	C7—H7B	0.9900
C1—C6	1.391 (2)	C10—C11	1.352 (2)
C1—C2	1.398 (2)	C10—H10A	0.9500
C1—C7	1.5116 (17)	C11—H11B	0.9500
C9—S1—C11	88.74 (7)	C1—C6—H6A	119.4
C8—N1—C9	122.90 (11)	C5—C6—H6A	119.4
C8—N1—H1A	118.5	C1—C7—C8	111.93 (11)
C9—N1—H1A	118.5	C1—C7—H7A	109.2
C9—N2—C10	109.29 (12)	C8—C7—H7A	109.2
C6—C1—C2	118.72 (12)	C1—C7—H7B	109.2
C6—C1—C7	122.39 (13)	C8—C7—H7B	109.2
C2—C1—C7	118.88 (14)	H7A—C7—H7B	107.9
C3—C2—C1	120.10 (15)	O1—C8—N1	122.09 (13)
C3—C2—H2A	119.9	O1—C8—C7	123.10 (11)
C1—C2—H2A	119.9	N1—C8—C7	114.80 (11)
C2—C3—C4	120.91 (13)	N2—C9—N1	120.89 (12)
C2—C3—Cl1	118.03 (13)	N2—C9—S1	115.75 (10)
C4—C3—Cl1	121.05 (10)	N1—C9—S1	123.35 (9)
C5—C4—C3	119.33 (12)	C11—C10—N2	115.89 (12)
C5—C4—Cl2	119.89 (13)	C11—C10—H10A	122.1
C3—C4—Cl2	120.78 (11)	N2—C10—H10A	122.1
C4—C5—C6	119.68 (15)	C10—C11—S1	110.32 (11)
C4—C5—H5A	120.2	C10—C11—H11B	124.8
C6—C5—H5A	120.2	S1—C11—H11B	124.8
C1—C6—C5	121.23 (13)
C6—C1—C2—C3	−1.4 (2)	C2—C1—C7—C8	−67.93 (18)
C7—C1—C2—C3	177.54 (14)	C9—N1—C8—O1	−0.4 (2)
C1—C2—C3—C4	0.2 (2)	C9—N1—C8—C7	−179.28 (13)
C1—C2—C3—Cl1	179.42 (11)	C1—C7—C8—O1	14.2 (2)
C2—C3—C4—C5	0.6 (2)	C1—C7—C8—N1	−166.90 (13)
Cl1—C3—C4—C5	−178.58 (12)	C10—N2—C9—N1	−179.19 (13)
C2—C3—C4—Cl2	−179.47 (12)	C10—N2—C9—S1	0.25 (17)
Cl1—C3—C4—Cl2	1.3 (2)	C8—N1—C9—N2	−175.45 (14)
C3—C4—C5—C6	−0.2 (2)	C8—N1—C9—S1	5.2 (2)
Cl2—C4—C5—C6	179.89 (12)	C11—S1—C9—N2	0.07 (12)
C2—C1—C6—C5	1.8 (2)	C11—S1—C9—N1	179.50 (13)
C7—C1—C6—C5	−177.07 (14)	C9—N2—C10—C11	−0.6 (2)
C4—C5—C6—C1	−1.0 (2)	N2—C10—C11—S1	0.62 (19)
C6—C1—C7—C8	110.97 (16)	C9—S1—C11—C10	−0.38 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2^i	0.88	2.03	2.8946 (16)	169

Symmetry code: (i) −x, −y+1, −z+1.