2-Chloro-N-(2,4-dichloro-phen-yl)-acetamide.

The structure of the title compound, C(8)H(6)Cl(3)NO, contains two mol-ecules in the asymmetric unit. In each independent mol-ecule, the conformation of the N-H bond is almost syn to the ortho-chloro substituent and the conformation of the C=O bond is anti to the N-H bond. The mol-ecules in the crystal structure are linked into supra-molecular chains through N-H⋯O hydrogen bonding along the a axis.

Related literature

For the preparation of the title compound, see: Shilpa & Gowda (2007 ▶); Pies et al. (1971 ▶). For related structures, see: Gowda, Foro & Fuess (2008 ▶); Gowda, Kožíšek et al. (2008 ▶); Gowda et al. (2009 ▶).

Experimental

Crystal data

C8H6Cl3NO

M = 238.49

Monoclinic,

a = 4.7457 (5) Å

b = 12.9266 (9) Å

c = 31.879 (4) Å

β = 90.12 (1)°

V = 1955.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.89 mm−1

T = 299 K

0.48 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur single-crystal diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.674, T max = 0.957

7393 measured reflections

3590 independent reflections

1475 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.196

S = 0.91

3590 reflections

241 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data 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/S1600536809018753/tk2452sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018753/tk2452Isup2.hkl

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

C8H6Cl3NO	F(000) = 960
Mr = 238.49	Dx = 1.620 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1466 reflections
a = 4.7457 (5) Å	θ = 2.5–27.8°
b = 12.9266 (9) Å	µ = 0.89 mm−1
c = 31.879 (4) Å	T = 299 K
β = 90.12 (1)°	Needle, colourless
V = 1955.6 (3) Å3	0.48 × 0.05 × 0.05 mm
Z = 8

Oxford Diffraction Xcalibur single-crystal diffractometer with a Sapphire CCD detector	3590 independent reflections
Radiation source: fine-focus sealed tube	1475 reflections with I > 2σ(I)
graphite	Rint = 0.077
Rotation method data acquisition using ω and φ scans	θmax = 25.3°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −5→4
Tmin = 0.674, Tmax = 0.957	k = −15→11
7393 measured reflections	l = −38→38

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ2(Fo2) + (0.0867P)2] where P = (Fo2 + 2Fc2)/3
3590 reflections	(Δ/σ)max = 0.005
241 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2007) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.5403 (4)	0.71319 (16)	0.00042 (6)	0.0507 (6)
Cl2	−0.1002 (5)	0.42476 (17)	0.07378 (7)	0.0699 (8)
Cl3	0.0189 (5)	1.14606 (18)	0.06668 (10)	0.0935 (9)
O1	−0.1586 (10)	0.9317 (4)	0.06073 (19)	0.0672 (18)
N1	0.2740 (11)	0.8593 (5)	0.06055 (18)	0.0362 (16)
H1N	0.460 (14)	0.876 (5)	0.0583 (19)	0.043*
C1	0.1840 (14)	0.7560 (5)	0.0644 (2)	0.0309 (17)
C2	0.2935 (13)	0.6804 (6)	0.0379 (2)	0.0330 (18)
C3	0.2098 (15)	0.5774 (6)	0.0412 (2)	0.0393 (19)
H3	0.2862	0.5270	0.0238	0.047*
C4	0.0105 (16)	0.5522 (6)	0.0710 (2)	0.047 (2)
C5	−0.0950 (15)	0.6242 (7)	0.0982 (2)	0.046 (2)
H5	−0.2243	0.6049	0.1186	0.055*
C6	−0.0095 (15)	0.7241 (6)	0.0950 (2)	0.044 (2)
H6	−0.0810	0.7727	0.1137	0.053*
C7	0.0950 (14)	0.9405 (6)	0.0596 (2)	0.0386 (19)
C8	0.2440 (16)	1.0429 (6)	0.0563 (3)	0.063 (3)
H8A	0.3208	1.0505	0.0283	0.075*
H8B	0.3997	1.0444	0.0761	0.075*
Cl4	1.0368 (4)	0.28731 (17)	0.25087 (6)	0.0545 (6)
Cl5	0.4118 (6)	0.60945 (19)	0.20155 (8)	0.0830 (8)
Cl6	0.4903 (4)	−0.11251 (17)	0.16628 (7)	0.0586 (6)
O2	0.3241 (10)	0.1017 (4)	0.1770 (2)	0.0701 (18)
N2	0.7526 (12)	0.1738 (5)	0.1816 (2)	0.0422 (18)
H2N	0.912 (15)	0.163 (6)	0.181 (2)	0.051*
C9	0.6701 (14)	0.2773 (6)	0.1861 (2)	0.0335 (17)
C10	0.7879 (14)	0.3385 (6)	0.2170 (2)	0.0381 (19)
C11	0.7131 (15)	0.4406 (6)	0.2217 (2)	0.045 (2)
H11	0.7958	0.4811	0.2425	0.054*
C12	0.5141 (17)	0.4817 (6)	0.1952 (3)	0.049 (2)
C13	0.3952 (15)	0.4215 (7)	0.1645 (3)	0.049 (2)
H13	0.2595	0.4499	0.1469	0.059*
C14	0.4723 (15)	0.3210 (6)	0.1595 (2)	0.044 (2)
H14	0.3922	0.2817	0.1381	0.052*
C15	0.5757 (15)	0.0933 (6)	0.1774 (2)	0.0374 (19)
C16	0.7204 (15)	−0.0104 (6)	0.1735 (3)	0.062 (3)
H16A	0.8307	−0.0229	0.1986	0.074*
H16B	0.8496	−0.0079	0.1500	0.074*

	U11	U22	U33	U12	U13	U23
Cl1	0.0426 (12)	0.0541 (13)	0.0555 (13)	−0.0074 (10)	0.0135 (9)	−0.0047 (11)
Cl2	0.0955 (19)	0.0486 (15)	0.0657 (16)	−0.0266 (12)	−0.0015 (13)	0.0074 (12)
Cl3	0.0723 (18)	0.0432 (15)	0.165 (3)	0.0070 (13)	0.0398 (16)	0.0038 (16)
O1	0.018 (3)	0.043 (4)	0.140 (6)	0.002 (3)	0.005 (3)	−0.001 (3)
N1	0.016 (3)	0.034 (4)	0.058 (4)	−0.007 (3)	0.001 (3)	0.000 (3)
C1	0.029 (4)	0.030 (4)	0.034 (4)	0.006 (3)	−0.006 (3)	−0.002 (4)
C2	0.029 (4)	0.045 (5)	0.025 (4)	0.000 (3)	0.003 (3)	0.006 (4)
C3	0.040 (5)	0.028 (5)	0.050 (5)	0.002 (4)	0.003 (4)	−0.004 (4)
C4	0.049 (5)	0.051 (6)	0.040 (5)	−0.012 (4)	−0.012 (4)	0.004 (4)
C5	0.037 (5)	0.055 (6)	0.046 (5)	−0.015 (4)	0.013 (4)	0.002 (5)
C6	0.047 (5)	0.050 (6)	0.036 (5)	0.004 (4)	0.012 (4)	−0.007 (4)
C7	0.021 (4)	0.035 (5)	0.060 (5)	0.003 (4)	−0.001 (4)	−0.008 (4)
C8	0.033 (5)	0.043 (5)	0.113 (8)	−0.002 (4)	0.007 (4)	0.001 (5)
Cl4	0.0407 (12)	0.0626 (15)	0.0602 (13)	0.0013 (10)	−0.0087 (9)	−0.0003 (12)
Cl5	0.106 (2)	0.0461 (15)	0.097 (2)	0.0256 (14)	−0.0060 (15)	−0.0084 (14)
Cl6	0.0516 (13)	0.0489 (13)	0.0753 (16)	−0.0065 (11)	−0.0020 (11)	−0.0133 (12)
O2	0.020 (3)	0.047 (4)	0.143 (6)	0.010 (3)	−0.003 (3)	−0.013 (4)
N2	0.020 (3)	0.042 (4)	0.064 (4)	0.002 (3)	0.000 (3)	−0.003 (3)
C9	0.028 (4)	0.036 (5)	0.037 (4)	0.000 (3)	0.008 (3)	0.001 (4)
C10	0.031 (4)	0.043 (5)	0.041 (5)	−0.001 (4)	−0.001 (3)	0.001 (4)
C11	0.045 (5)	0.043 (5)	0.047 (5)	−0.003 (4)	0.000 (4)	−0.008 (4)
C12	0.054 (6)	0.044 (5)	0.051 (5)	0.012 (4)	0.011 (4)	0.001 (5)
C13	0.043 (5)	0.054 (6)	0.049 (5)	0.007 (4)	−0.007 (4)	0.006 (5)
C14	0.043 (5)	0.041 (5)	0.046 (5)	0.005 (4)	−0.004 (4)	0.004 (4)
C15	0.022 (4)	0.045 (5)	0.045 (5)	0.002 (4)	0.001 (3)	−0.005 (4)
C16	0.035 (5)	0.040 (5)	0.110 (8)	−0.004 (4)	−0.001 (5)	−0.003 (5)

Cl1—C2	1.728 (7)	Cl4—C10	1.730 (7)
Cl2—C4	1.731 (8)	Cl5—C12	1.733 (8)
Cl3—C8	1.740 (8)	Cl6—C16	1.728 (8)
O1—C7	1.209 (7)	O2—C15	1.199 (7)
N1—C7	1.350 (9)	N2—C15	1.344 (9)
N1—C1	1.407 (9)	N2—C9	1.401 (9)
N1—H1N	0.91 (7)	N2—H2N	0.77 (7)
C1—C2	1.392 (9)	C9—C10	1.381 (9)
C1—C6	1.403 (9)	C9—C14	1.385 (9)
C2—C3	1.393 (10)	C10—C11	1.376 (10)
C3—C4	1.381 (10)	C11—C12	1.373 (10)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.367 (11)	C12—C13	1.371 (10)
C5—C6	1.358 (10)	C13—C14	1.360 (11)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.505 (11)	C15—C16	1.511 (10)
C8—H8A	0.9700	C16—H16A	0.9700
C8—H8B	0.9700	C16—H16B	0.9700
C7—N1—C1	123.3 (6)	C15—N2—C9	125.1 (6)
C7—N1—H1N	115 (4)	C15—N2—H2N	118 (6)
C1—N1—H1N	122 (4)	C9—N2—H2N	117 (6)
C2—C1—C6	117.4 (7)	C10—C9—C14	118.4 (7)
C2—C1—N1	119.9 (6)	C10—C9—N2	120.5 (6)
C6—C1—N1	122.6 (6)	C14—C9—N2	121.1 (6)
C1—C2—C3	121.2 (6)	C11—C10—C9	121.6 (7)
C1—C2—Cl1	120.1 (6)	C11—C10—Cl4	118.3 (6)
C3—C2—Cl1	118.7 (6)	C9—C10—Cl4	120.1 (6)
C4—C3—C2	118.2 (7)	C12—C11—C10	118.8 (7)
C4—C3—H3	120.9	C12—C11—H11	120.6
C2—C3—H3	120.9	C10—C11—H11	120.6
C5—C4—C3	121.8 (7)	C13—C12—C11	120.1 (7)
C5—C4—Cl2	120.3 (7)	C13—C12—Cl5	120.6 (6)
C3—C4—Cl2	117.9 (7)	C11—C12—Cl5	119.3 (7)
C6—C5—C4	119.4 (7)	C14—C13—C12	121.1 (7)
C6—C5—H5	120.3	C14—C13—H13	119.4
C4—C5—H5	120.3	C12—C13—H13	119.4
C5—C6—C1	121.8 (7)	C13—C14—C9	120.0 (7)
C5—C6—H6	119.1	C13—C14—H14	120.0
C1—C6—H6	119.1	C9—C14—H14	120.0
O1—C7—N1	123.5 (7)	O2—C15—N2	123.6 (7)
O1—C7—C8	123.5 (7)	O2—C15—C16	122.1 (7)
N1—C7—C8	112.9 (6)	N2—C15—C16	114.3 (6)
C7—C8—Cl3	111.9 (5)	C15—C16—Cl6	113.6 (5)
C7—C8—H8A	109.2	C15—C16—H16A	108.8
Cl3—C8—H8A	109.2	Cl6—C16—H16A	108.8
C7—C8—H8B	109.2	C15—C16—H16B	108.8
Cl3—C8—H8B	109.2	Cl6—C16—H16B	108.8
H8A—C8—H8B	107.9	H16A—C16—H16B	107.7
C7—N1—C1—C2	132.9 (7)	C15—N2—C9—C10	132.3 (8)
C7—N1—C1—C6	−48.9 (10)	C15—N2—C9—C14	−48.6 (10)
C6—C1—C2—C3	1.3 (9)	C14—C9—C10—C11	0.0 (10)
N1—C1—C2—C3	179.6 (6)	N2—C9—C10—C11	179.2 (7)
C6—C1—C2—Cl1	−178.2 (5)	C14—C9—C10—Cl4	−179.8 (5)
N1—C1—C2—Cl1	0.1 (8)	N2—C9—C10—Cl4	−0.7 (9)
C1—C2—C3—C4	1.2 (10)	C9—C10—C11—C12	0.7 (11)
Cl1—C2—C3—C4	−179.4 (5)	Cl4—C10—C11—C12	−179.5 (6)
C2—C3—C4—C5	−3.0 (11)	C10—C11—C12—C13	−0.5 (12)
C2—C3—C4—Cl2	178.1 (5)	C10—C11—C12—Cl5	178.6 (6)
C3—C4—C5—C6	2.3 (11)	C11—C12—C13—C14	−0.5 (12)
Cl2—C4—C5—C6	−178.9 (6)	Cl5—C12—C13—C14	−179.5 (6)
C4—C5—C6—C1	0.4 (11)	C12—C13—C14—C9	1.3 (12)
C2—C1—C6—C5	−2.1 (10)	C10—C9—C14—C13	−1.0 (11)
N1—C1—C6—C5	179.7 (7)	N2—C9—C14—C13	179.9 (7)
C1—N1—C7—O1	−2.1 (12)	C9—N2—C15—O2	0.2 (12)
C1—N1—C7—C8	178.6 (6)	C9—N2—C15—C16	−179.5 (7)
O1—C7—C8—Cl3	14.0 (11)	O2—C15—C16—Cl6	2.5 (11)
N1—C7—C8—Cl3	−166.8 (5)	N2—C15—C16—Cl6	−177.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.91 (7)	1.95 (7)	2.851 (7)	170 (6)
N2—H2N···O2i	0.77 (7)	2.11 (7)	2.872 (7)	168 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.91 (7)	1.95 (7)	2.851 (7)	170 (6)
N2—H2N⋯O2i	0.77 (7)	2.11 (7)	2.872 (7)	168 (8)

Symmetry code: (i) .