2-Chloro-N-(3-chloro-phen-yl)acetamide.

The N-H bond in the title compound, C(8)H(7)Cl(2)NO, is anti to the meta-chloro substituent in the aromatic ring in both independent mol-ecules comprising the asymmetric unit. The C=O bond is anti to the N-H bond and is also anti to the methyl-ene H atoms. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains.

Related literature

For preparation and characterisation of the compound, see: Pies et al. (1971 ▶), Gowda et al. (2006 ▶). For related structures, see: Gowda et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

C8H7Cl2NO

M = 204.05

Orthorhombic,

a = 4.897 (1) Å

b = 17.379 (3) Å

c = 21.484 (4) Å

V = 1828.4 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.66 mm−1

T = 299 K

0.45 × 0.08 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.756, T max = 0.987

10213 measured reflections

3179 independent reflections

1745 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.094

wR(F 2) = 0.103

S = 1.23

3179 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1206 Friedel pairs

Flack parameter: 0.04 (13)

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/S1600536809011660/tk2407sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011660/tk2407Isup2.hkl

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

C8H7Cl2NO	F(000) = 832
Mr = 204.05	Dx = 1.483 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2170 reflections
a = 4.897 (1) Å	θ = 2.2–27.3°
b = 17.379 (3) Å	µ = 0.66 mm−1
c = 21.484 (4) Å	T = 299 K
V = 1828.4 (6) Å3	Needle, colourless
Z = 8	0.45 × 0.08 × 0.02 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3179 independent reflections
Radiation source: fine-focus sealed tube	1745 reflections with I > 2σ(I)
graphite	Rint = 0.074
Rotation method data acquisition using ω and φ scans	θmax = 25.3°, θmin = 2.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −5→5
Tmin = 0.756, Tmax = 0.987	k = −20→20
10213 measured reflections	l = −25→23

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)] = 0.094	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0084P)2 + 1.6742P] where P = (Fo2 + 2Fc2)/3
S = 1.23	(Δ/σ)max = 0.005
3179 reflections	Δρmax = 0.36 e Å−3
217 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 1206 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (13)

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	0.6906 (6)	0.02452 (11)	−0.05228 (9)	0.1205 (10)
Cl2	−0.0094 (4)	0.03432 (10)	0.27874 (9)	0.0775 (6)
O1	0.3155 (10)	0.0159 (2)	0.16486 (19)	0.0612 (14)
N1	0.5179 (11)	0.1333 (3)	0.1663 (2)	0.0466 (14)
H1N	0.5335	0.1741	0.1887	0.056*
C1	0.6654 (15)	0.1331 (3)	0.1102 (3)	0.0429 (17)
C2	0.6148 (14)	0.0817 (3)	0.0628 (3)	0.052 (2)
H2	0.4813	0.0441	0.0673	0.063*
C3	0.7641 (19)	0.0868 (4)	0.0088 (3)	0.065 (2)
C4	0.9656 (17)	0.1404 (5)	0.0005 (4)	0.071 (2)
H4	1.0676	0.1422	−0.0360	0.086*
C5	1.0113 (16)	0.1917 (5)	0.0482 (4)	0.076 (2)
H5	1.1442	0.2295	0.0436	0.091*
C6	0.8643 (15)	0.1880 (4)	0.1025 (3)	0.059 (2)
H6	0.8996	0.2229	0.1343	0.071*
C7	0.3544 (15)	0.0775 (4)	0.1898 (3)	0.0451 (18)
C8	0.2235 (15)	0.1014 (3)	0.2507 (3)	0.062 (2)
H8A	0.1310	0.1502	0.2449	0.074*
H8B	0.3655	0.1089	0.2816	0.074*
Cl3	0.3476 (5)	0.13531 (10)	0.41715 (9)	0.0882 (7)
Cl4	−0.7058 (4)	0.32439 (10)	0.17867 (9)	0.0819 (7)
O2	−0.2983 (9)	0.2490 (2)	0.25851 (18)	0.0523 (12)
N2	−0.1818 (11)	0.3561 (2)	0.3135 (2)	0.0484 (14)
H2N	−0.2216	0.4041	0.3169	0.058*
C9	0.0161 (13)	0.3283 (4)	0.3558 (3)	0.0400 (16)
C10	0.0721 (13)	0.2514 (4)	0.3645 (3)	0.0468 (18)
H10	−0.0243	0.2138	0.3430	0.056*
C11	0.2759 (15)	0.2317 (4)	0.4062 (3)	0.0484 (19)
C12	0.4158 (14)	0.2849 (4)	0.4398 (3)	0.058 (2)
H12	0.5517	0.2702	0.4676	0.069*
C13	0.3504 (17)	0.3615 (4)	0.4315 (3)	0.069 (2)
H13	0.4408	0.3989	0.4547	0.083*
C14	0.1548 (16)	0.3833 (4)	0.3897 (3)	0.057 (2)
H14	0.1150	0.4351	0.3841	0.068*
C15	−0.3165 (14)	0.3176 (4)	0.2684 (3)	0.0442 (16)
C16	−0.4892 (14)	0.3714 (3)	0.2297 (3)	0.0599 (19)
H16A	−0.3697	0.4050	0.2061	0.072*
H16B	−0.5973	0.4033	0.2573	0.072*

	U11	U22	U33	U12	U13	U23
Cl1	0.221 (3)	0.0728 (13)	0.0674 (14)	−0.0099 (18)	0.0240 (19)	−0.0174 (12)
Cl2	0.0703 (15)	0.0686 (12)	0.0935 (15)	−0.0124 (13)	0.0192 (14)	0.0007 (12)
O1	0.089 (4)	0.030 (2)	0.064 (3)	−0.017 (3)	0.007 (3)	−0.011 (2)
N1	0.060 (4)	0.031 (3)	0.049 (4)	−0.009 (3)	0.001 (3)	−0.008 (3)
C1	0.051 (5)	0.031 (4)	0.046 (4)	0.005 (4)	−0.001 (4)	0.000 (4)
C2	0.058 (6)	0.041 (4)	0.058 (5)	0.005 (4)	0.005 (4)	0.006 (4)
C3	0.090 (7)	0.044 (4)	0.061 (5)	0.005 (5)	0.003 (5)	0.008 (4)
C4	0.071 (6)	0.083 (6)	0.061 (6)	0.019 (6)	0.012 (5)	0.013 (5)
C5	0.055 (6)	0.094 (7)	0.080 (6)	−0.016 (5)	0.007 (6)	0.022 (6)
C6	0.047 (5)	0.063 (5)	0.069 (6)	−0.011 (5)	−0.015 (5)	0.004 (4)
C7	0.050 (5)	0.034 (4)	0.051 (4)	−0.001 (4)	−0.012 (4)	0.000 (4)
C8	0.079 (6)	0.047 (4)	0.059 (5)	−0.008 (4)	0.013 (5)	−0.007 (3)
Cl3	0.125 (2)	0.0597 (12)	0.0799 (14)	0.0279 (14)	−0.0236 (14)	0.0066 (11)
Cl4	0.0896 (16)	0.0693 (12)	0.0869 (14)	0.0000 (13)	−0.0394 (13)	−0.0053 (11)
O2	0.061 (3)	0.032 (2)	0.064 (3)	0.006 (3)	−0.012 (3)	−0.009 (2)
N2	0.056 (4)	0.031 (3)	0.058 (4)	0.007 (3)	−0.009 (3)	−0.013 (3)
C9	0.037 (4)	0.043 (4)	0.040 (4)	0.000 (4)	−0.004 (4)	−0.006 (4)
C10	0.053 (5)	0.035 (4)	0.052 (4)	−0.003 (4)	0.002 (4)	−0.001 (3)
C11	0.055 (5)	0.050 (4)	0.040 (4)	0.012 (4)	0.004 (4)	0.005 (3)
C12	0.049 (6)	0.073 (5)	0.051 (5)	0.000 (4)	−0.007 (4)	−0.003 (4)
C13	0.079 (6)	0.061 (5)	0.066 (6)	−0.007 (5)	−0.011 (5)	−0.016 (4)
C14	0.067 (6)	0.049 (4)	0.055 (5)	0.007 (5)	−0.009 (4)	−0.006 (4)
C15	0.046 (4)	0.040 (4)	0.047 (4)	0.010 (4)	−0.004 (4)	−0.001 (4)
C16	0.059 (5)	0.050 (4)	0.071 (5)	−0.001 (4)	−0.029 (5)	−0.011 (4)

Cl1—C3	1.739 (7)	Cl3—C11	1.728 (6)
Cl2—C8	1.738 (6)	Cl4—C16	1.730 (6)
O1—C7	1.212 (6)	O2—C15	1.215 (6)
N1—C7	1.354 (7)	N2—C15	1.349 (7)
N1—C1	1.406 (7)	N2—C9	1.415 (7)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.373 (8)	C9—C10	1.376 (7)
C1—C2	1.376 (7)	C9—C14	1.380 (8)
C2—C3	1.375 (8)	C10—C11	1.384 (8)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.369 (9)	C11—C12	1.359 (8)
C4—C5	1.376 (9)	C12—C13	1.381 (8)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.373 (9)	C13—C14	1.366 (8)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.516 (8)	C15—C16	1.510 (8)
C8—H8A	0.9700	C16—H16A	0.9700
C8—H8B	0.9700	C16—H16B	0.9700
C7—N1—C1	128.4 (5)	C15—N2—C9	128.9 (5)
C7—N1—H1N	115.8	C15—N2—H2N	115.6
C1—N1—H1N	115.8	C9—N2—H2N	115.6
C6—C1—C2	119.3 (6)	C10—C9—C14	120.2 (6)
C6—C1—N1	117.8 (6)	C10—C9—N2	123.7 (6)
C2—C1—N1	122.9 (7)	C14—C9—N2	116.1 (6)
C1—C2—C3	119.1 (7)	C9—C10—C11	118.1 (6)
C1—C2—H2	120.5	C9—C10—H10	120.9
C3—C2—H2	120.5	C11—C10—H10	120.9
C4—C3—C2	122.5 (7)	C12—C11—C10	122.6 (6)
C4—C3—Cl1	118.3 (7)	C12—C11—Cl3	119.0 (6)
C2—C3—Cl1	119.1 (7)	C10—C11—Cl3	118.3 (6)
C3—C4—C5	117.4 (8)	C11—C12—C13	118.1 (7)
C3—C4—H4	121.3	C11—C12—H12	121.0
C5—C4—H4	121.3	C13—C12—H12	121.0
C6—C5—C4	121.2 (8)	C14—C13—C12	120.9 (7)
C6—C5—H5	119.4	C14—C13—H13	119.5
C4—C5—H5	119.4	C12—C13—H13	119.5
C5—C6—C1	120.4 (7)	C13—C14—C9	120.0 (7)
C5—C6—H6	119.8	C13—C14—H14	120.0
C1—C6—H6	119.8	C9—C14—H14	120.0
O1—C7—N1	124.1 (6)	O2—C15—N2	125.2 (6)
O1—C7—C8	123.8 (6)	O2—C15—C16	123.5 (6)
N1—C7—C8	112.1 (5)	N2—C15—C16	111.3 (5)
C7—C8—Cl2	113.2 (4)	C15—C16—Cl4	113.6 (4)
C7—C8—H8A	108.9	C15—C16—H16A	108.8
Cl2—C8—H8A	108.9	Cl4—C16—H16A	108.8
C7—C8—H8B	108.9	C15—C16—H16B	108.8
Cl2—C8—H8B	108.9	Cl4—C16—H16B	108.8
H8A—C8—H8B	107.8	H16A—C16—H16B	107.7
C7—N1—C1—C6	−165.6 (6)	C15—N2—C9—C10	−11.4 (10)
C7—N1—C1—C2	15.7 (10)	C15—N2—C9—C14	169.1 (6)
C6—C1—C2—C3	−0.3 (9)	C14—C9—C10—C11	−2.2 (9)
N1—C1—C2—C3	178.4 (6)	N2—C9—C10—C11	178.3 (5)
C1—C2—C3—C4	1.1 (10)	C9—C10—C11—C12	1.9 (9)
C1—C2—C3—Cl1	−177.3 (5)	C9—C10—C11—Cl3	−179.8 (5)
C2—C3—C4—C5	−1.6 (11)	C10—C11—C12—C13	−0.1 (10)
Cl1—C3—C4—C5	176.8 (6)	Cl3—C11—C12—C13	−178.4 (5)
C3—C4—C5—C6	1.3 (11)	C11—C12—C13—C14	−1.4 (11)
C4—C5—C6—C1	−0.6 (11)	C12—C13—C14—C9	1.1 (11)
C2—C1—C6—C5	0.0 (10)	C10—C9—C14—C13	0.7 (10)
N1—C1—C6—C5	−178.7 (6)	N2—C9—C14—C13	−179.7 (6)
C1—N1—C7—O1	1.8 (10)	C9—N2—C15—O2	3.9 (11)
C1—N1—C7—C8	−177.8 (6)	C9—N2—C15—C16	−174.2 (5)
O1—C7—C8—Cl2	−4.6 (9)	O2—C15—C16—Cl4	10.9 (9)
N1—C7—C8—Cl2	175.0 (4)	N2—C15—C16—Cl4	−170.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.15	2.962 (6)	157
N2—H2N···O1ii	0.86	2.04	2.892 (6)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.15	2.962 (6)	157
N2—H2N⋯O1ii	0.86	2.04	2.892 (6)	174

Symmetry codes: (i) ; (ii) .