2-Chloro-N-(3,5-dimethyl­phen­yl)acetamide

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

doi:10.1107/S160053680901304X

. 2009 Apr 18;65(Pt 5):o1040. doi: 10.1107/S160053680901304X

2-Chloro-N-(3,5-dimethylphenyl)acetamide

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

PMCID: PMC2977723 PMID: 21583859

Abstract

The conformation of the C=O bond in the structure of the title compound, C₁₀H₁₂ClNO, is anti to the N—H bond and to the C—Cl bond in the side chain in all four independent molecules comprising the asymmetric unit. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into supramolecular chains

Related literature

For details of the preparation of the title compound, see: Shilpa & Gowda (2007 ▶). For related structures, see: Gowda et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

C₁₀H₁₂ClNO
M _r = 197.66
Orthorhombic,
a = 25.9770 (1) Å
b = 9.7698 (4) Å
c = 16.0578 (7) Å
V = 4075.3 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 299 K
0.45 × 0.42 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.864, T _max = 0.906
27845 measured reflections
7450 independent reflections
4868 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.164
S = 1.04
7450 reflections
478 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.20 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/S160053680901304X/tk2414sup1.cif

e-65-o1040-sup1.cif^{(30.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901304X/tk2414Isup2.hkl

e-65-o1040-Isup2.hkl^{(364.5KB, 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⋯O4ⁱ	0.86	2.14	2.983 (4)	168
N2—H2N⋯O3ⁱⁱ	0.86	2.12	2.975 (4)	171
N3—H3N⋯O2ⁱⁱⁱ	0.86	2.15	3.000 (4)	170
N4—H4N⋯O1^iv	0.86	2.13	2.987 (4)	172

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

supplementary crystallographic information

Comment

In the present work, as part of a study of substituent effects on the crystal structures of aromatic amides (Gowda et al., 2008a,b,c), the structure of 2-chloro-N-(3,5-dimethylphenyl)acetamide (I) has been determined. The conformation of the C=O bond in (I) is anti to the N—H bond and to the C–Cl bond in the side chain (Fig. 1), in all the four independent molecules comprising the asymmetric unit. This is consistent with the anti conformation of the C=O bond to the N—H bond and to the side chain methylene H-atoms in 2-chloro-N- (2,4-dimethylphenyl)acetamide (Gowda et al., 2008a), in 2-chloro-N-(3,5-dichlorophenyl)acetamide (Gowda et al., 2008b), and in 2-chloro-N-(3-methylphenyl)acetamide (Gowda et al., 2008c). The molecules in (I) are linked into infinite chains through intermolecular N—H···O hydrogen bonding (Table 1, Fig. 2). There are two independent supramolecular chains, one comprising O2- and O3- containing molecules, and the other comprising O1- and O4-containing molecules.

Experimental

Compound (I) was prepared according to the literature method (Shilpa and Gowda, 2007). Single crystals were obtained from the slow evaporation of an ethanolic solution of (I).