2-Chloro-N-(2,5-dichloro-phen-yl)acetamide.

The conformation of the N-H bond in the structure of the title compound, C(8)H(6)Cl(3)NO, is anti to the C=O bond. The N-H H atom shows close intra-molecular N-H⋯Cl hydrogen bonds with both the ring Cl atom in the ortho position and the side-chain Cl atom. The mol-ecules crystallize in planes parallel to (221).

Related literature

For the preparation, see: Shilpa & Gowda (2007 ▶); Pies et al. (1971 ▶). For our work on the effect of ring and side-chain substitutions on the solid-state geometries of aromatic amides, see: Gowda Foro & Fuess (2008 ▶); Gowda, Kožíšek et al. (2008 ▶); Gowda et al. (2009 ▶).

Experimental

Crystal data

C8H6Cl3NO

M = 238.49

Triclinic,

a = 7.492 (2) Å

b = 8.496 (2) Å

c = 8.988 (2) Å

α = 69.68 (2)°

β = 67.54 (2)°

γ = 66.67 (2)°

V = 472.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.92 mm−1

T = 299 K

0.38 × 0.28 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.720, T max = 0.823

2735 measured reflections

1914 independent reflections

1359 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.02

1914 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019898/bt2962sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019898/bt2962Isup2.hkl

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

C8H6Cl3NO	Z = 2
Mr = 238.49	F(000) = 240
Triclinic, P1	Dx = 1.677 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.492 (2) Å	Cell parameters from 698 reflections
b = 8.496 (2) Å	θ = 3.2–27.9°
c = 8.988 (2) Å	µ = 0.92 mm−1
α = 69.68 (2)°	T = 299 K
β = 67.54 (2)°	Prism, colourless
γ = 66.67 (2)°	0.38 × 0.28 × 0.22 mm
V = 472.4 (2) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1914 independent reflections
Radiation source: fine-focus sealed tube	1359 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −8→9
Tmin = 0.720, Tmax = 0.823	k = −10→9
2735 measured reflections	l = −10→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.1195P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1914 reflections	Δρmax = 0.28 e Å−3
122 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (4)

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	1.03470 (12)	0.29507 (9)	−0.22746 (8)	0.0527 (2)
Cl2	0.72031 (12)	0.28513 (10)	0.52153 (8)	0.0594 (3)
Cl3	0.68240 (12)	0.81217 (11)	−0.40685 (9)	0.0608 (3)
O1	0.4705 (3)	0.7757 (2)	0.0703 (2)	0.0531 (6)
N1	0.7131 (3)	0.5825 (3)	−0.0831 (3)	0.0375 (5)
H1N	0.772 (4)	0.572 (3)	−0.178 (3)	0.045*
C1	0.7880 (4)	0.4371 (3)	0.0367 (3)	0.0322 (6)
C2	0.9420 (4)	0.2924 (3)	−0.0178 (3)	0.0335 (6)
C3	1.0238 (4)	0.1464 (3)	0.0928 (3)	0.0389 (6)
H3	1.1261	0.0506	0.0548	0.047*
C4	0.9541 (4)	0.1425 (3)	0.2590 (3)	0.0395 (6)
H4	1.0076	0.0443	0.3343	0.047*
C5	0.8036 (4)	0.2866 (3)	0.3124 (3)	0.0376 (6)
C6	0.7181 (4)	0.4339 (3)	0.2045 (3)	0.0370 (6)
H6	0.6158	0.5290	0.2436	0.044*
C7	0.5703 (4)	0.7374 (3)	−0.0617 (3)	0.0343 (6)
C8	0.5319 (4)	0.8743 (3)	−0.2174 (3)	0.0436 (7)
H8A	0.5540	0.9800	−0.2190	0.052*
H8B	0.3905	0.9042	−0.2109	0.052*

	U11	U22	U33	U12	U13	U23
Cl1	0.0643 (5)	0.0476 (4)	0.0356 (4)	−0.0068 (4)	−0.0059 (3)	−0.0184 (3)
Cl2	0.0708 (5)	0.0553 (5)	0.0319 (4)	0.0043 (4)	−0.0182 (3)	−0.0098 (3)
Cl3	0.0635 (5)	0.0648 (5)	0.0333 (4)	−0.0041 (4)	−0.0140 (3)	−0.0049 (3)
O1	0.0577 (13)	0.0443 (11)	0.0350 (10)	0.0045 (10)	−0.0100 (10)	−0.0104 (9)
N1	0.0410 (13)	0.0352 (12)	0.0268 (11)	−0.0026 (10)	−0.0082 (10)	−0.0081 (9)
C1	0.0309 (13)	0.0310 (13)	0.0336 (13)	−0.0067 (11)	−0.0102 (10)	−0.0079 (10)
C2	0.0337 (13)	0.0358 (14)	0.0321 (13)	−0.0114 (11)	−0.0053 (11)	−0.0126 (11)
C3	0.0341 (14)	0.0336 (14)	0.0468 (16)	−0.0013 (11)	−0.0138 (12)	−0.0146 (12)
C4	0.0402 (15)	0.0333 (14)	0.0431 (15)	−0.0042 (12)	−0.0196 (12)	−0.0060 (11)
C5	0.0394 (15)	0.0384 (14)	0.0327 (13)	−0.0063 (12)	−0.0129 (11)	−0.0090 (11)
C6	0.0356 (14)	0.0358 (14)	0.0338 (13)	−0.0018 (11)	−0.0105 (11)	−0.0111 (11)
C7	0.0334 (14)	0.0313 (13)	0.0352 (14)	−0.0073 (11)	−0.0095 (11)	−0.0077 (11)
C8	0.0405 (15)	0.0421 (15)	0.0369 (15)	−0.0039 (13)	−0.0109 (12)	−0.0062 (12)

Cl1—C2	1.737 (2)	C3—C4	1.374 (4)
Cl2—C5	1.737 (3)	C3—H3	0.9300
Cl3—C8	1.771 (3)	C4—C5	1.379 (4)
O1—C7	1.212 (3)	C4—H4	0.9300
N1—C7	1.348 (3)	C5—C6	1.383 (3)
N1—C1	1.410 (3)	C6—H6	0.9300
N1—H1N	0.82 (3)	C7—C8	1.518 (3)
C1—C6	1.389 (3)	C8—H8A	0.9700
C1—C2	1.395 (3)	C8—H8B	0.9700
C2—C3	1.382 (3)
C7—N1—C1	128.8 (2)	C4—C5—C6	122.2 (2)
C7—N1—H1N	117.0 (19)	C4—C5—Cl2	119.14 (19)
C1—N1—H1N	114.0 (19)	C6—C5—Cl2	118.7 (2)
C6—C1—C2	119.1 (2)	C5—C6—C1	118.8 (2)
C6—C1—N1	122.9 (2)	C5—C6—H6	120.6
C2—C1—N1	117.9 (2)	C1—C6—H6	120.6
C3—C2—C1	120.9 (2)	O1—C7—N1	125.7 (2)
C3—C2—Cl1	119.2 (2)	O1—C7—C8	117.8 (2)
C1—C2—Cl1	119.91 (19)	N1—C7—C8	116.5 (2)
C4—C3—C2	120.1 (2)	C7—C8—Cl3	115.98 (18)
C4—C3—H3	120.0	C7—C8—H8A	108.3
C2—C3—H3	120.0	Cl3—C8—H8A	108.3
C3—C4—C5	119.0 (2)	C7—C8—H8B	108.3
C3—C4—H4	120.5	Cl3—C8—H8B	108.3
C5—C4—H4	120.5	H8A—C8—H8B	107.4
C7—N1—C1—C6	0.5 (4)	C3—C4—C5—Cl2	−178.1 (2)
C7—N1—C1—C2	−178.1 (3)	C4—C5—C6—C1	−0.7 (4)
C6—C1—C2—C3	0.6 (4)	Cl2—C5—C6—C1	178.5 (2)
N1—C1—C2—C3	179.3 (2)	C2—C1—C6—C5	−0.1 (4)
C6—C1—C2—Cl1	−178.90 (19)	N1—C1—C6—C5	−178.7 (2)
N1—C1—C2—Cl1	−0.2 (3)	C1—N1—C7—O1	−4.4 (5)
C1—C2—C3—C4	−0.2 (4)	C1—N1—C7—C8	175.9 (2)
Cl1—C2—C3—C4	179.3 (2)	O1—C7—C8—Cl3	179.7 (2)
C2—C3—C4—C5	−0.6 (4)	N1—C7—C8—Cl3	−0.5 (3)
C3—C4—C5—C6	1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl3	0.82 (3)	2.43 (3)	2.922 (2)	120 (2)
N1—H1N···Cl1	0.82 (3)	2.45 (3)	2.933 (2)	119 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl3	0.82 (3)	2.43 (3)	2.922 (2)	120 (2)
N1—H1N⋯Cl1	0.82 (3)	2.45 (3)	2.933 (2)	119 (2)