N-(2,6-Dimethyl­phen­yl)benzamide

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

doi:10.1107/S1600536808018230

. 2008 Jun 19;64(Pt 7):o1299. doi: 10.1107/S1600536808018230

N-(2,6-Dimethylphenyl)benzamide

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

PMCID: PMC2961710 PMID: 21202928

Abstract

The title compound, C₁₅H₁₅NO, crystallizes with two molecules in the asymmetric unit. The H—N—C=O units are in a trans conformation, similar to that observed in N-(3,4-dimethylphenyl)benzamide, N-(2,6-dichlorophenyl)benzamide and other benzanilides. The central –NHCO– bridging unit is tilted at angles of 17.1 (3) and 16.4 (3)° to the benzoyl ring in the two molecules. The two rings (benzoyl and aniline) are almost orthogonal with respect to each other, making dihedral angles of 86.3 (1) and 86.0 (1)° in the two molecules. N—H⋯O hydrogen bonds link molecules into infinite chains running along the c axis.

Related literature

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

Experimental

Crystal data

C₁₅H₁₅NO
M _r = 225.28
Monoclinic,
a = 16.4389 (8) Å
b = 8.2903 (4) Å
c = 9.4902 (3) Å
β = 98.165 (4)°
V = 1280.25 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 (2) K
0.52 × 0.46 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.924, T _max = 0.985
38015 measured reflections
2504 independent reflections
2110 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.108
S = 0.98
2504 reflections
307 parameters
35 restraints
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018230/bt2724sup1.cif

e-64-o1299-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018230/bt2724Isup2.hkl

e-64-o1299-Isup2.hkl^{(120.5KB, 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	0.86	2.19	2.949 (2)	147
N2—H2N⋯O2ⁱⁱ	0.86	2.17	2.949 (2)	150

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds (Interreg IIIA) for financial support in the purchase of the diffractometer.

supplementary crystallographic information

Comment

In the present work, the structure of N-(2,6-dimethylphenyl)-benzamide (N26DMPBA) has been determined to study the effect of substituents on the solid state geometries of benzanilides (Gowda et al., 2003; Gowda et al., 2008a; Gowda et al., 2008b). The conformations of the N—H and C=O bonds in N26DMPBA (Fig.1) are anti to each other, similar to that observed in N-(3,4-dimethylphenyl)-benzamide (Gowda et al., 2008a), N-(2,6-dichlorophenyl)-benzamide (Gowda et al., 2008b) and other benzanilides (Gowda et al., 2003). The structure of N26DMPBA has two molecules in its asymmetric unit. The central amide group –NHCO– is tilted to the benzoyl ring at the angles of 17.1 (3)° and 16.4 (3)°, in molecule 1 and 2, respectively. The two rings (benzoyl and aniline) are almost orthogonal, with the dihedral angles of 86.3 (1)° and 86.0 (1)° in molecules 1 and 2, respectively.

Part of the crystal structure of the title compound showing molecular chains as viewed down the b axis is shown in Fig.2. Hydrogen bonds N1–H1N···O1(i) and N2–H2N···O2(ii) give rise to infinite molecular chains running along the c axis (Symmetry codes: (i) x,-y,z + 1/2; (ii) x,-y + 1,z + 1/2).

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.