N-(3,4-Dimethyl­phen­yl)acetamide

B Thimme Gowda; Sabine Foro; Hartmut Fuess

doi:10.1107/S1600536807060916

. 2007 Dec 6;64(Pt 1):o11. doi: 10.1107/S1600536807060916

N-(3,4-Dimethylphenyl)acetamide

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

PMCID: PMC2914973 PMID: 21200674

Abstract

The conformation of the N—H bond in the title compound (34DMPA), C₁₀H₁₃NO, is syn to the 3-methyl substituent in the aromatic ring, in contrast to the anti conformation observed with respect to the 3-chloro substituent in N-(3,4-dichlorophenyl)acetamide (34DCPA). The asymmetric unit of the structure contains three molecules. The bond parameters in 34DMPA are similar to those in 34DCPA, N-(2,6-dimethylphenyl)acetamide, N-(3,5-dimethylphenyl)acetamide and other acetanilides. The molecules in 34DMPA are linked into infinite chains through N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Gowda et al. (2007a ▶,b ▶); Gowda, Kozisek, Svoboda & Fuess (2007 ▶); Gowda, Kožíšek, Tokarčík & Fuess (2007 ▶); Jones et al. (1990 ▶); Shilpa & Gowda (2007 ▶).

Experimental

Crystal data

C₁₀H₁₃NO
M _r = 163.21
Triclinic,
a = 6.749 (1) Å
b = 14.281 (2) Å
c = 15.005 (2) Å
α = 85.33 (1)°
β = 79.81 (1)°
γ = 87.58 (1)°
V = 1418.1 (3) Å³
Z = 6
Cu Kα radiation
μ = 0.59 mm⁻¹
T = 299 (2) K
0.35 × 0.33 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
5528 measured reflections
5025 independent reflections
3386 reflections with I > 2σ(I)
R _int = 0.044
3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.210
S = 1.03
5025 reflections
344 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060916/lw2051sup1.cif

e-64-00o11-sup1.cif^{(24.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060916/lw2051Isup2.hkl

e-64-00o11-Isup2.hkl^{(246.1KB, 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⋯O3	0.88 (3)	2.08 (3)	2.956 (3)	177 (3)
N3—H3N⋯O2	0.86 (3)	2.14 (3)	2.989 (3)	172 (3)
N2—H2N⋯O1ⁱ	0.98 (3)	1.92 (3)	2.893 (3)	170 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

B.T.G. thanks the Alexander von Humboldt Foundation, Bonn, Germany for extensions of his research fellowship.

supplementary crystallographic information

Comment

In the present work, the structure of N-(3,4-dimethylphenyl)-acetamide (34DMPA) has been determined to study the effect of substituents on the structures of N-aromatic amides (Gowda et al., 2007a, b; Gowda, Kozisek, Svoboda & Fuess, 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007). The conformation of the N—H bond in 34DMPA is syn to the 3-methyl substituent in the aromatic ring, in contrast to the anti conformation obseved with respect to the 3-chloro substituent in N-(3,4-dichlorophenyl)-acetamide (34DCPA) (Jones et al., 1990). The asymmetric unit of the structure contains 3 molecules. The bond parameters in 34DMPA are similar to those in 34DCPA (Jones et al., 1990), N-(2,6-dimethylphenyl)-acetamide (Gowda et al., 2007b), N-(3,5-dimethylphenyl)-acetamide (Gowda, Kožíšek, Tokarčík & Fuess, 2007) and other acetanilides. The molecules in 34DMPA are linked into chains through N—H···O hydrogen bonding (Table 1 & Fig. 2).

Experimental

The title compound was prepared according to the literature method (Shilpa and 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 and Gowda, 2007). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.