3-Methyl-N-phen­ylbenzamide

B Thimme Gowda; Sabine Foro; B P Sowmya; Hartmut Fuess

doi:10.1107/S1600536808008143

. 2008 Mar 29;64(Pt 4):o770. doi: 10.1107/S1600536808008143

3-Methyl-N-phenylbenzamide

B Thimme Gowda ^a,^*, Sabine Foro ^b, B P Sowmya ^a, Hartmut Fuess ^b

PMCID: PMC2961009 PMID: 21202157

Abstract

The conformation of the C=O bond in the structure of the title compound, C₁₄H₁₃NO, is anti to the meta-methyl substituent in the benzoyl ring. The conformations of the N—H and C=O bonds in the amide group are also anti to each other. The asymmetric unit of the structure contains two molecules. The bond parameters are similar to those in N-(phenyl)benzamide, 2-methyl-N-(phenyl)benzamide and other benzanilides. The amide group –NHCO– forms dihedral angles of 20.97 (34) and 45.65 (19)° with the benzoyl rings, and 41.54 (25) and 31.87 (29)° with the aniline rings, in the two independent molecules. The benzoyl and aniline rings adopt dihedral angles of 22.17 (18) and 75.86 (12)° in the two independent molecules. In the crystal structure, molecules are linked into chains by intermolecular N—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₄H₁₃NO
M _r = 211.25
Monoclinic,
a = 16.947 (2) Å
b = 15.531 (1) Å
c = 8.623 (1) Å
β = 93.35 (1)°
V = 2265.7 (4) Å³
Z = 8
Cu Kα radiation
μ = 0.62 mm⁻¹
T = 299 (2) K
0.60 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD4 diffractometer
Absorption correction: none
4339 measured reflections
4039 independent reflections
2466 reflections with I > 2σ(I)
R _int = 0.034
3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F ² > 2σ(F ²)] = 0.082
wR(F ²) = 0.240
S = 1.03
4039 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008143/dn2328sup1.cif

e-64-0o770-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008143/dn2328Isup2.hkl

e-64-0o770-Isup2.hkl^{(198KB, 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	2.16	2.968 (4)	157
N2—H2N⋯O2ⁱⁱ	0.86	2.01	2.853 (3)	168

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions to his research fellowship.

supplementary crystallographic information

Comment

As part of a study of the substituent effects on the structures of benzanilides, in the present work, the structure of 3-methyl-N-(phenyl)benzamide (NP3MBA) has been determined (Gowda et al., 2003, 2008a,b).

The asymmetric unit of the structure of NP3MBA contains two molecules (Fig. 1). The conformation of the C═O bonds are anti to the meta-methyl substituents in the benzoyl phenyl rings. The conformations of the N—H and C═O bonds in the –NH—CO– groups are also anti to each other. The bond parameters in NP3MBA are similar to those in N-(phenyl)benzamide, 2-methyl-N-(phenyl)benzamide and other benzanilides (Gowda et al., 2003, 2008a,b). The amide group –NHCO– forms the dihedral angles of 20.97 (34)° (molecule 1) and 45.65(0.19) (molecule 2) with the benzoyl ring, and 41.54 (25)° (molecule 1), 31.87(0.29) (molecule 2) with the aniline ring. The benzoyl and the aniline rings have the dihedral angles of 22.17 (18)°) (molecule 1) and 75.86(0.12) (molecule 2).

The packing diagram of NP3MBA molecules showing the hydrogen bonds N1—H1N···O1, N2—H2N···O2 (Table 1) involved in the formation of molecular chain is shown in Fig. 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.