N-(3-Methyl­phen­yl)benzamide

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

doi:10.1107/S1600536808035186

. 2008 Oct 31;64(Pt 11):o2247. doi: 10.1107/S1600536808035186

N-(3-Methylphenyl)benzamide

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

PMCID: PMC2959694 PMID: 21581101

Abstract

The asymmetric unit of the title compound, C₁₄H₁₃NO, contains four molecules, which are linked through N—H⋯O hydrogen bonds into two symmetry-independent chains running parallel to [001] and [101]. The N—H and C=O bonds of the amide groups are trans oriented in all four molecules. The molecules are not planar and both aromatic rings are twisted strongly relative to the plane of the amide group. The dihedral angle between the two benzene rings ranges from 70.6 (2) to 74.2 (2)°. The N—H bond is anti to the meta-methyl substituent in the aniline fragment in three of the four symmetry-independent molecules. In the fourth molecule, the aniline unit is disordered over two nearly coplanar positions; the anti and syn conformers occupy the same site in the crystal with equal probability.

Related literature

For the general procedure for the synthesis of the title compound, see: Gowda et al. (2003 ▶). For structure of the 3-chlorophenyl analogue, see: Gowda et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₃NO
M _r = 211.25
Monoclinic,
a = 13.269 (2) Å
b = 53.686 (6) Å
c = 9.3921 (12) Å
β = 134.21 (1)°
V = 4795.7 (10) Å³
Z = 16
Cu Kα radiation
μ = 0.58 mm⁻¹
T = 299 (2) K
0.43 × 0.25 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
9315 measured reflections
4168 independent reflections
3197 reflections with I > 2σ(I)
R _int = 0.028
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.129
S = 1.03
4168 reflections
653 parameters
110 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; 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 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035186/gk2174sup1.cif

e-64-o2247-sup1.cif^{(37.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035186/gk2174Isup2.hkl

e-64-o2247-Isup2.hkl^{(204.3KB, 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⋯O2ⁱ	0.87 (3)	1.96 (3)	2.822 (4)	168 (4)
N2—H2N⋯O1	0.84 (3)	2.06 (3)	2.848 (4)	156 (5)
N3—H3N⋯O4ⁱⁱ	0.86 (3)	2.00 (3)	2.829 (4)	163 (4)
N4—H4N⋯O3ⁱ	0.82 (3)	2.04 (3)	2.813 (4)	156 (5)

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extension of his research fellowship.

supplementary crystallographic information

Comment

In the present work, the structure of N-(3-methylphenyl)-benzamide (N3MPBA) has been determined to explore the effect of substituents on the structures of benzanilides (Gowda et al., 2003, 2008). The conformations of N—H and C=O bonds in the amide group of N3MPBA are trans to each other (Fig.1 ). Further, the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline fragment, similar to that observed in N-(3-chlorophenyl)-benzamide (N3CPBA). The asymmetric unit of the structure contains four molecules. Aniline fragment in one of the molecules is disordered. The amide group –NHCO– forms dihedral angles of 24.4 (9)°, 22.3 (13)°, 22.7 (16)°, 25.2 (11)° with the benzoyl fragments, in the molecules 1, 2, 3, 4, respectively, compared to the value of 18.2 (2)° in N3CPBA (Gowda et al., 2008). The dihedral angles between the two benzene rings (benzoyl and aniline fragments) in the four molecules are 70.8 (1)°, 70.6 (2)°, 73.3 (3)° and 74.2 (2)° for the molecules 1, 2, 3, 4, respectively, compared to the value of 61.0 (1)°.in N3CPBA. In the crystal structure, the molecules are linked into a chain through intermolecular N—H···O hydrogen bonds (Table 1 and 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.