2-Methyl-N-phenyl­benzamide

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

doi:10.1107/S1600536807068821

. 2008 Jan 9;64(Pt 2):o383. doi: 10.1107/S1600536807068821

2-Methyl-N-phenylbenzamide

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

PMCID: PMC2960230 PMID: 21201413

Abstract

In the structure of the title compound (NP2MBA), C₁₄H₁₃NO, the conformation of the C—O bond is syn to the ortho-methyl substituent in the benzoyl phenyl ring, while the N—H bond is anti to the ortho-methyl substituent. The structure of NP2MBA closely resembles that of 2-chloro-N-phenylbenzamide, with similar bond parameters. The dihedral angle between the phenyl and benzoyl rings is 88.05 (5)°. Molecules are linked into a chain through N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

C₁₄H₁₃NO
M _r = 211.25
Orthorhombic,
a = 14.404 (1) Å
b = 8.6824 (6) Å
c = 18.710 (1) Å
V = 2339.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 (2) K
0.40 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007 ▶) T _min = 0.970, T _max = 0.981
11005 measured reflections
2387 independent reflections
1686 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.115
S = 1.05
2387 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); 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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXS97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068821/dn2308sup1.cif

e-64-0o383-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068821/dn2308Isup2.hkl

e-64-0o383-Isup2.hkl^{(117.4KB, 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	0.878 (17)	2.012 (18)	2.8751 (16)	167.7 (15)

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Symmetry code: (i) Inline graphic .

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of 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 2-methyl-N-(phenyl)benzamide (NP2MBA) has been determined (Gowda, et al., 2003; 2007; 2008). In the structure of NP2MBA,(Fig. 1), the conformation of the C—O bond is syn to the ortho-methyl substituent in the benzoyl phenyl ring, while the N—H bond is anti to the ortho-methyl substituent. The bond parameters in NP2MBA are similar to those in 2-chloro-N-(phenyl)-benzamide (Gowda, et al.,2003), 2-chloro-N-(2-chlorophenyl)-benzamide (Gowda, et al.,2007), N-(4-methylphenyl)-benzamide (Gowda, et al.,2008) and other benzanilides. The dihedral angle between the phenyl and benzoyl rings in NP2MBA is 88.05 (5)°. The packing diagram of NP2MBA molecules showing the hydrogen bonds N1—H1N···O1 (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.