2-Chloro-N-(2,5-dichloro­phen­yl)acetamide

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

doi:10.1107/S1600536809019898

. 2009 May 29;65(Pt 6):o1445. doi: 10.1107/S1600536809019898

2-Chloro-N-(2,5-dichlorophenyl)acetamide

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

PMCID: PMC2969621 PMID: 21583283

Abstract

The conformation of the N—H bond in the structure of the title compound, C₈H₆Cl₃NO, is anti to the C=O bond. The N—H H atom shows close intramolecular N—H⋯Cl hydrogen bonds with both the ring Cl atom in the ortho position and the side-chain Cl atom. The molecules 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 _r = 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
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.31 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/S1600536809019898/bt2962sup1.cif

e-65-o1445-sup1.cif^{(14.9KB, cif)}

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

e-65-o1445-Isup2.hkl^{(94.2KB, 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⋯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)

Open in a new tab

Acknowledgments

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

supplementary crystallographic information

Comment

As part of a study of the effect of ring and side chain substitutions on the solid state geometries of aromatic amides (Gowda Foro & Fuess, 2008; Gowda, Kožíšek et al., 2008; Gowda et al., 2009), in the present work, the structure of 2-chloro-N-(2,5-dichlorophenyl)acetamide (25DCPCA)(I) has been determined. The conformation of the N—H bond in the structure (Fig. 1) is syn to the ortho-chloro and anti to the meta-chloro substituents in the aromatic ring, in contrast to the syn conformation observed with respect to both the 2-chloro and 3-chloro groups in 2-chloro-N-(2,3-dichlorophenyl)acetamide (Gowda, Kožíšek et al., 2008). Furthermore, the conformation of the C=O bond is anti to both the N—H bond and side chain Cl atom, compared to the anti conformation of the C=O bond with respect to the N–H bond and syn with respect to the side chain Cl atom, observed in 2-chloro-N-(2,3-dichlorophenyl)-acetamide (Gowda Foro & Fuess, 2008). But the conformations of the N–H bond and the side chain C–H bonds are anti to each other, while those of the ring C–Cl and the side chain C–Cl bonds are syn to each other. Further, the N—H H-atom shows simultaneous intramolecular hydrogen bonding with both the ring and side chain Cl atoms. The crystal packing is shown in Fig.2 (Table 1).

Experimental

The title compound 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 the title compound used for X-ray diffraction studies were grown by a slow evaporation of its ethanolic solution at room temperature.