2-Chloro-N-(2,4-dichloro­phen­yl)­acetamide

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

doi:10.1107/S1600536809018753

. 2009 May 23;65(Pt 6):o1367. doi: 10.1107/S1600536809018753

2-Chloro-N-(2,4-dichlorophenyl)acetamide

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

PMCID: PMC2969726 PMID: 21583217

Abstract

The structure of the title compound, C₈H₆Cl₃NO, contains two molecules in the asymmetric unit. In each independent molecule, 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 molecules in the crystal structure are linked into supramolecular 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 _r = 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
Δρ_max = 0.44 e Å⁻³
Δρ_min = −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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018753/tk2452sup1.cif

e-65-o1367-sup1.cif^{(18.9KB, cif)}

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

e-65-o1367-Isup2.hkl^{(176KB, 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⋯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)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extension of his research fellowship.

supplementary crystallographic information

Comment

As part of a study into the effect of ring- and side-chain substitutions on the solid-state structures of aromatic amides (Gowda, Foro & Fuess, 2008; Gowda, Kožíšek et al., 2008; Gowda et al., 2009), in the present work the structure of the title compound (I) is described. There are two independent molecules in the asymmetric unit of (I), Fig. 1. The conformation of the N—H bond in each independent molecule is almost syn to the ortho-chloro substituent, similar to the syn conformation observed with respect to both the 2-chloro and 3-chloro substituents in 2-chloro-N-(2,3-dichlorophenyl)acetamide (Gowda et al., 2008a). The conformation of the C=O bond is anti to the N—H bond, also similar to that observed in 2-chloro-N-(2,3-dichlorophenyl)acetamide. The N1–H1N···O1 and N2–H2N···O2 hydrogen bonding pack the molecules into supramolecular chains aligned along the a direction (Table 1, Fig. 2).

Experimental

Compound (I) was prepared according to the literature method (Shilpa & Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared, NMR and NQR spectra (Shilpa & Gowda, 2007; Pies et al., 1971). Single crystals of were grown by the slow evaporation of an ethanol solution of (I) held at room temperature.