N-(2,3-Dimethyl­phen­yl)-2,2,2-trimethyl­acetamide

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

doi:10.1107/S1600536809021229

. 2009 Jun 10;65(Pt 7):o1529. doi: 10.1107/S1600536809021229

N-(2,3-Dimethylphenyl)-2,2,2-trimethylacetamide

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

PMCID: PMC2969287 PMID: 21582819

Abstract

The N—H bond in the title compound, C₁₃H₁₉NO, is anti to the C=O bond and is also anti to both the 2- and 3-methyl substituents in the aromatic ring. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains propagating along the c axis.

Related literature

For the preparation of the title compound, see: Shilpa & Gowda (2007 ▶). For related structures, see: Gowda et al. (2007a ▶,b ▶,c ▶). graphic file with name e-65-o1529-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₉NO
M _r = 205.29
Monoclinic,
a = 18.276 (4) Å
b = 8.227 (2) Å
c = 8.633 (2) Å
β = 97.94 (2)°
V = 1285.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 299 K
0.45 × 0.16 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.971, T _max = 0.992
4295 measured reflections
2349 independent reflections
1214 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.221
S = 0.96
2349 reflections
195 parameters
112 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021229/ci2806sup1.cif

e-65-o1529-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021229/ci2806Isup2.hkl

e-65-o1529-Isup2.hkl^{(115.5KB, 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⋯O1ⁱ	0.94	2.11	2.966 (3)	151

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

As part of a study of the effect of ring and side chain substitutions on the crystal structures of chemically and biologically important class of compounds such as aromatic amides (Gowda et al., 2007a, b, c), the crystal structure of 2,2,2-trimethyl-N-(2,3-dimethylphenyl)-acetamide has been determined.

The conformation of the N–H bond in the title compound is anti to both the 2- and 3-methyl substituents in the aromatic ring (Fig. 1), in contrast to the syn conformation observed with respect to both the 2- and 3-chloro substituents in 2,2,2-trimethyl-N-(2,3-dichlorophenyl)acetamide (Gowda et al., 2007a), syn conformation with respect to the 2-methyl substituent in 2,2,2-trimethyl-N- (2-methylphenyl)acetamide (Gowda et al., 2007b) and anti conformation with respect to 3-methyl substituent in 2,2,2-trimethyl-N- (3-methylphenyl)acetamide (Gowda et al., 2007c). Furthermore, the conformation of the C═O bond is anti to the N—H bond in the amide segment.

In the title compound, the molecules are linked into chains (Fig. 2) running along the c axis by intermolecular N—H···O hydrogen bonds (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 and NMR spectra (Shilpa & Gowda, 2007). Single crystals of the title compound were grown by slow evaporation of its ethanolic solution at room temperature.