N-(2,3-Dimethyl­phen­yl)-4-methylbenzamide

Vinola Z Rodrigues; Peter Herich; B Thimme Gowda; Jozef Kožíšek

doi:10.1107/S1600536811034490

. 2011 Aug 27;67(Pt 9):o2463. doi: 10.1107/S1600536811034490

N-(2,3-Dimethylphenyl)-4-methylbenzamide

Vinola Z Rodrigues ^a, Peter Herich ^b, B Thimme Gowda ^a,^*, Jozef Kožíšek ^b

PMCID: PMC3200728 PMID: 22059024

Abstract

In the molecule of the title compound, C₁₆H₁₇NO, the two aromatic rings are almost perpendicular to each other [dihedral angle 85.90 (5)°]. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds which link the molecules, forming C(4) chains running along the c axis.

Related literature

For preparation of the title compound, see: Gowda et al. (2003 ▶). For the study of the effect of substituents on the structures and other aspects of N-(aryl)amides, see: Arjunan et al. (2004 ▶); Bhat & Gowda (2000 ▶); Bowes et al. (2003 ▶); Gowda et al. (2009 ▶); Rodrigues et al. (2011 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₇NO
M _r = 239.31
Monoclinic,
a = 8.1723 (3) Å
b = 19.3923 (7) Å
c = 9.3170 (3) Å
β = 111.781 (4)°
V = 1371.14 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.76 × 0.12 × 0.09 mm

Data collection

Oxford Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶) based on Clark & Reid (1995 ▶)] T _min = 0.989, T _max = 0.994
21529 measured reflections
3806 independent reflections
1925 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.126
S = 0.93
3806 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 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: DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034490/bt5622sup1.cif

e-67-o2463-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034490/bt5622Isup2.hkl

e-67-o2463-Isup2.hkl^{(174.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034490/bt5622Isup3.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⋯O1ⁱ	0.86	2.20	2.9256 (12)	143

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Symmetry code: (i) Inline graphic .

Acknowledgments

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship. PH and JK thank the Grant Agencies for their financial support: the VEGA Grant Agency of the Slovak Ministry of Education (grant No. 1/0679/11), the Research and Development Agency (Slovakia) (grant No. APVV-0202-10), and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

supplementary crystallographic information

Comment

The structural aspects of N-aryl amides are of interest due to their chemical and biological importance (Arjunan et al., 2004; Bhat & Gowda, 2000; Bowes et al., 2003; Gowda et al., 2003; 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., 2003, 2009; Rodrigues et al., 2011), the structure of 4-methyl-N-(2,3-dimethylphenyl)benzamide (I) has been determined (Fig. 1). In the crystal, the ortho- and meta-methyl substituents in the anilino ring are positioned anti to the N—H bond, similar to that observed in one of the molecules of 4-methyl-N-(2-methylphenyl)benzamide (II) (Rodrigues et al., 2011).

The central amide group –NHCO– is tilted to the anilino ring with the C10—C9—N1—C1 and C14—C9—N1—C1 torsion angles of -63.4 (2)° and 118.1 (1)°. The C3—C2—C1—N1 and C7—C2—C1—N1 torsion angles are -24.4 (2)° and 156.8 (1)°, respectively, while the C3—C2—C1—O1 and C7—C2—C1—O1 torsion angles are 155.6 (1)° and -23.2 (2)°, respectively. But the C2—C1—N1—C9 and C9—N1—C1—O1 torsion angles are -179.5 (1)° and 0.5 (2)°, respectively.

The packing of molecules linked by N—H···O hydrogen bonds 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. Cuboid-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.