2-Chloro-N-(3-chloro­phen­yl)acetamide

B Thimme Gowda; Sabine Foro; Hiromitsu Terao; Hartmut Fuess

doi:10.1107/S1600536809011660

. 2009 Apr 2;65(Pt 5):o949. doi: 10.1107/S1600536809011660

2-Chloro-N-(3-chlorophenyl)acetamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, Hiromitsu Terao ^c, Hartmut Fuess ^b

PMCID: PMC2977650 PMID: 21583993

Abstract

The N—H bond in the title compound, C₈H₇Cl₂NO, is anti to the meta-chloro substituent in the aromatic ring in both independent molecules comprising the asymmetric unit. The C=O bond is anti to the N—H bond and is also anti to the methylene H atoms. Intermolecular N—H⋯O hydrogen bonds link the molecules into supramolecular 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 _r = 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
Δρ_max = 0.36 e Å⁻³
Δρ_min = −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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011660/tk2407sup1.cif

e-65-0o949-sup1.cif^{(18.4KB, cif)}

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

e-65-0o949-Isup2.hkl^{(156KB, hkl)}

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

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

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

As part of a study of the effect of ring and side-chain substitutions on the solid-state geometry of aromatic amides (Gowda et al., 2008a, b, c), in the present work the structure of 2-chloro-N-(3-chlorophenyl)acetamide (I) has been determined. The N—H bond is anti to the meta-chloro substituent in the aromatic ring (Fig. 1), similar to that observed in N-(3-chlorophenyl)acetamide (Gowda et al., 2008a), but in contrast to the syn conformations observed with respect to the meta-methyl group in 2-chloro-N-(3-methylphenyl)acetamide (Gowda et al., 2008c) and with respect to both chloro substituents in 2-chloro-N-(2,3-dichlorophenyl)acetamide (Gowda et al., 2008b). Further, the C=O bond is not only anti to the N—H bond but also to the methylene-H-atoms. The asymmetric unit of the structure contains two molecules that are orthogonal to each other. The molecules in (I) are linked into infinite chains through intermolecular N1—H1···O2 and N2—H2—O1 hydrogen bonding (Table 1) as viewed down the a-axis (Fig. 2).

Experimental

Compound (I) was prepared according to the literature method (Gowda et al., 2006). The purity of (I) was checked by determining its melting point and characterised by recording its infrared, NMR and NQR spectra (Gowda et al., 2006 & Pies et al., 1971). Single crystals of (I) were obtained from an ethanolic solution held at room temperature.