N-(2,3-Dimethyl­phen­yl)benzamide

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

doi:10.1107/S1600536809012112

. 2009 Apr 8;65(Pt 5):o965. doi: 10.1107/S1600536809012112

N-(2,3-Dimethylphenyl)benzamide

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

PMCID: PMC2977665 PMID: 21584008

Abstract

The conformation of the N—H bond in the structure of the title compound, C₁₅H₁₅NO, is anti to the ortho and meta-methyl substituents in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho and meta-chloro substituents in N-(2,3-dichlorophenyl)benzamide. Furthermore, the conformations of N—H and C=O bonds in the amide group are anti to each other, similar to those observed in other benzanilides. The dihedral angle between the benzoyl and aniline rings is 84.1 (2)°. The amide group is twisted by 23.0 (3)° out of the plane of the benzoyl ring. The structure exhibits positional disorder over the aniline ring, with site occupancies of 0.80 (1) and 0.20 (1) for the major and minor components, respectively. In the crystal, molecules are connected through N—H⋯O hydrogen bonds into chains running along the b axis. An intramolecular C—H⋯O close contact occurs.

Related literature

For related structures, see Azumaya et al. (1994 ▶); Gowda et al. (2003 ▶, 2007 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C₁₅H₁₅NO
M _r = 225.28
Orthorhombic,
a = 8.4656 (2) Å
b = 9.4848 (2) Å
c = 31.0957 (9) Å
V = 2496.81 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.52 × 0.16 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.963, T _max = 0.996
48994 measured reflections
2409 independent reflections
1572 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.146
S = 1.05
2409 reflections
222 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.14 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/S1600536809012112/dn2440sup1.cif

e-65-0o965-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012112/dn2440Isup2.hkl

e-65-0o965-Isup2.hkl^{(116KB, 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	0.883 (16)	2.028 (17)	2.907 (2)	173 (2)
C14—H14C⋯N1	0.96	2.39	2.852 (4)	109

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Symmetry code: (i) Inline graphic .

Acknowledgments

MT 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.

supplementary crystallographic information

Comment

As part of our continuing efforts to explore the effect of substituents on the solid state geometries of benzanilides (Gowda et al., 2003, 2007, 2008a,b), in the present work, the structure of N-(2,3-dimethylphenyl)benzamide (N23DMPBA) has been determined. The conformation of the N—H bond in N23DMPBA is anti to both the ortho and meta-methyl substituents in the aniline benzene ring (Fig. 1), in contrast to the syn conformations observed with respect to both the ortho and meta-chloro substituents in N-(2,3-dichlorophenyl)benzamide (N23DCPBA)(Gowda et al., 2007), while the conformations of the N—H and C=O bonds in the amide group of N23DMPBA are anti to each other, similar to that observed in N23DCPBA, N-(2,6-dimethylphenyl)benzamide (Azumaya et al., 1994; Gowda et al., 2008b), N-(3,4-dimethylphenyl)benzamide (Gowda et al., 2008a) and other benzanilides (Gowda et al., 2003). In the crystal structure, the N—H···O hydrogen bonds link the molecules into chains running along the b axis (Table 1 & Fig. 2), while the structure is stabilized by C—H···N intramolecular hydrogen bond with atom C14 as donor and atom N1 as acceptor. The atoms of anilino ring (including the methyl groups) are positionally disordered (Fig. 3) with site occupancy factor 0.80 for major component (atoms C8 to C15) and 0.20 for minor component (C8d to C15d). The disordered orientations of anilino ring are essentially planar, forming a dihedral angle of 1.5 (7)°. The dihedral angle between the benzoyl and anilino ring (major) is 84.1 (2)°. The amido group is twisted by 23.0 (3)° out of the plane of benzoyl ring.

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 ethanol solution and used for X-ray diffraction studies at room temperature.