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

Vinola Z Rodrigues; Marek Fronc; B Thimme Gowda; Jozef Kožíšek

doi:10.1107/S1600536811018770

. 2011 May 25;67(Pt 6):o1500. doi: 10.1107/S1600536811018770

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

Vinola Z Rodrigues ^a, Marek Fronc ^b, B Thimme Gowda ^a,^*, Jozef Kožíšek ^b

PMCID: PMC3120561 PMID: 21754867

Abstract

The asymmetric unit of the title compound, C₁₅H₁₅NO, contains two independent molecules, which differ in the dihedral angle between the aromatic rings [48.98 (9) and 57.48 (8)°]. The methyl groups in para positions are disordered over two equally occupied positions. An intramolecular N—H⋯O hydrogen bond occurs. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds which link the molecules into chains running along the b axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For our study of the effect of substituents on the structures and other aspects of N-(aryl)-amides, see: Bhat & Gowda (2000 ▶); Bowes et al. (2003 ▶); Gowda et al. (2008 ▶, 2009 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C₁₅H₁₅NO
M _r = 225.28
Triclinic,
a = 7.2964 (6) Å
b = 9.9075 (5) Å
c = 18.1347 (13) Å
α = 88.331 (5)°
β = 82.892 (6)°
γ = 79.558 (5)°
V = 1279.29 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.88 × 0.09 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T _min = 0.968, T _max = 0.996
18269 measured reflections
4354 independent reflections
1602 reflections with I > 2σ(I)
R _int = 0.088

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.097
S = 0.74
4354 reflections
311 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018770/bt5550sup1.cif

e-67-o1500-sup1.cif^{(25.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018770/bt5550Isup2.hkl

e-67-o1500-Isup2.hkl^{(213.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018770/bt5550Isup3.cml

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—H1A⋯O2	0.86	2.05	2.878 (2)	163
N2—H2A⋯O1ⁱ	0.86	2.05	2.883 (2)	162

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Symmetry code: (i) Inline graphic .

Acknowledgments

MF and JK thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship.

supplementary crystallographic information

Comment

The structural aspects of N-aryl amides are of interest due to their chemical and biological importance (Bhat & Gowda, 2000; Bowes et al., 2003; Gowda et al., 2008, 2009; Saeed et al., 2010). In the present work, as part of a study of the substituent effects on the structures of benzanilides (Gowda, et al., 2008, 2009), the structure of 4-methyl-N-(2-methylphenyl)benzamide (I) has been determined (Fig.1). The asymmetric unit of (I) contains two independent molecules. In the crystal, the ortho-methyl substituent in the anilino ring is positioned syn to the N–H bond in one of the molecules and anti in the other molecule. Further, the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other in both the molecules, similar to that observed in 2-methyl-N-(4-methylphenyl)benzamide (II)(Gowda et al., 2008) and 4-methyl-N-(2,6-dimethylphenyl)benzamide (III) (Gowda et al., 2009) and, with similar bond parameters.

The central amide group –NHCO– is tilted to the anilino ring with the C2—C1—N1—C8 and C6—C1—N1—C8 torsion angles of -118.2 (3)° and 63.9 (3)° in molecule 1, and the C17—C16—N2—C23 and C21—C16—N2—C23 torsion angles of -86.8 (3)° and 97.6 (3)° in molecule 2, while the C10—C9—C8—N1 and C14—C9—C8—N1 torsion angles in molecule 1, and and the C25—C24—C23—N2 and C29—C24—C23—N2 torsion angles in molecule 2 are -13.4 (4)° and 171.7 (2)°, and -150.4 (2)° and 27.9 (4)°, respectively.

The packing of molecules linked by N—H···O hydrogen bonds into infinite chains is shown in Fig. 2.

Experimental

The title compound was prepared according to the method described by 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. needle-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.