2-Methyl-N-(3-methyl­phen­yl)benzamide

B Thimme Gowda; Sabine Foro; B P Sowmya; Hartmut Fuess

doi:10.1107/S1600536808003103

. 2008 Jan 30;64(Pt 2):o541. doi: 10.1107/S1600536808003103

2-Methyl-N-(3-methylphenyl)benzamide

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

PMCID: PMC2960197 PMID: 21201560

Abstract

In the structure of the title compound (N3MP2MBA), C₁₅H₁₅NO, the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring and that of the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, while the conformations of the N—H and C=O bonds are anti to each other. The bond parameters in N3MP2MBA are similar to those in 2-methyl-N-phenylbenzamide, N-(3,4-dimethylphenyl)benzamide and other benzanilides. The amide group, –NHCO–, makes a dihedral angle of 55.2 (7)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 36.2 (1)°. N—H⋯O hydrogen bonds give rise to infinite chains running along the b axis of the crystal structure.

Related literature

For related literature, see: Gowda et al. (2003 ▶; 2008a ▶,b ▶).

Experimental

Crystal data

C₁₅H₁₅NO
M _r = 225.28
Tetragonal,
a = 8.931 (2) Å
c = 15.816 (4) Å
V = 1261.5 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.58 mm⁻¹
T = 299 (2) K
0.55 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
1606 measured reflections
1168 independent reflections
1096 reflections with I > 2σ(I)
R _int = 0.016
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.100
S = 1.07
1168 reflections
158 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003103/om2212sup1.cif

e-64-0o541-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003103/om2212Isup2.hkl

e-64-0o541-Isup2.hkl^{(57.8KB, 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	0.837 (18)	2.10 (2)	2.908 (3)	163 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the structures of N-aromatic amides, in the present work, the structure of N-(3-methylphenyl)-2-methylbenzamide (N3MP2MBA) has been determined (Gowda et al., 2003; 2008a; 2008b). In the structure of N3MP2MBA (Fig. 1), the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring and that of the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, while the conformations of the N—H and C=O bonds are anti to each other. The bond parameters in N2MP2MBA are similar to those in N-(phenyl)-2-methylbenzamide (Gowda et al., 2008a), N-(3,4-dimethylphenyl)-benzamide (Gowda et al., 2008b) and other benzanilides (Gowda et al., 2003). The amide group –NHCO– has the dihedral angle of 55.2 (7)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 36.2 (1)°. The packing diagram of N3MP2MBA molecules showing the hydrogen bonds N1—H1N···O1 (Table 1) involved in the formation of molecular chain is given in Fig. 2.

Experimental

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.