N-(2,6-Dimethyl­phen­yl)-4-methyl­benzamide

B Thimme Gowda; Miroslav Tokarčík; Jozef Kožíšek; B P Sowmya; Hartmut Fuess

doi:10.1107/S1600536809022648

. 2009 Jun 17;65(Pt 7):o1612. doi: 10.1107/S1600536809022648

N-(2,6-Dimethylphenyl)-4-methylbenzamide

B Thimme Gowda ^a,^*, Miroslav Tokarčík ^b, Jozef Kožíšek ^b, B P Sowmya ^a, Hartmut Fuess ^c

PMCID: PMC2969511 PMID: 21582884

Abstract

In the molecular structure of the title compound, C₁₆H₁₇NO, the two aromatic rings are close to orthogonal to each other [dihedral angle 78.8 (1)°], while the central –NH—C(=O)– amide core is nearly coplanar with the benzoyl ring, forming a dihedral angle of 3.5 (2)°. Intermolecular N—H⋯O hydrogen bonds in the crystal structure link the molecules into infinite chains running along the c axis of the crystal, and a C—H⋯O interaction also occurs.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Gowda, Foro et al. (2008 ▶, 2009 ▶); Gowda, Tokarčík et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₇NO
M _r = 239.31
Tetragonal,
a = 16.6224 (5) Å
c = 19.9508 (7) Å
V = 5512.5 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.48 × 0.07 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.977, T _max = 0.992
17659 measured reflections
2649 independent reflections
1250 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.108
S = 0.99
2649 reflections
169 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022648/dn2462sup1.cif

e-65-o1612-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022648/dn2462Isup2.hkl

e-65-o1612-Isup2.hkl^{(127.7KB, 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	0.892 (13)	2.025 (14)	2.8814 (16)	160.6 (15)
C7—H7⋯O1ⁱ	0.93	2.48	3.385 (2)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship. MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the crystal structures of benzanilides (Gowda, Foro et al., 2008, 2009; Gowda, Tokarčík et al., 2008), in the present work, the structure of 4-methyl-N-(2,6-dimethylphenyl)benzamide (I) has been determined. The conformations of the N—H and C═O bonds in the amide segment of the structure are anti to each other (Fig.1), similar to that observed in 4-methyl-N-(phenyl)benzamide (Gowda, Foro et al., 2009), N-(2,6-dimethylphenyl)benzamide (Gowda, Tokarčík et al., 2008), 2-methyl-N-(2,6-dimethylphenyl)benzamide (Gowda, Foro et al., 2008) and other benzanilides, with similar bond parameters. The two aromatic rings in the structure of (I) make the dihedral angle of 78.8 (1)°, while the central amide core –NH—C(═O)– is nearly coplanar with the benzoyl ring, forming a dihedral angle of 3.5 (2)°. Part of the crystal structure of (I), showing the formation of hydrogen-bonded chains (Table 1) running in [001] direction 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.