N-(2-Methyl­phen­yl)-2-nitro­benzamide

Aamer Saeed; Shahid Hussain; Michael Bolte

doi:10.1107/S1600536808002298

. 2008 Jan 25;64(Pt 2):o521. doi: 10.1107/S1600536808002298

N-(2-Methylphenyl)-2-nitrobenzamide

Aamer Saeed ^a, Shahid Hussain ^a, Michael Bolte ^b,^*

PMCID: PMC2960181 PMID: 21201540

Abstract

In the title compound, C₁₄H₁₂N₂O₃, the dihedral angle between the two aromatic rings is 41.48 (5)°. The nitro group is twisted by 24.7 (3)° out of the plane of the aromatic ring to which it is attached. The molecules are connected by N—H⋯O hydrogen bonds into chains running along the a axis.

Related literature

For related literature, see: Igawa et al. (1999 ▶); Jackson et al. (1994 ▶); Makino et al. (2001 ▶, 2003 ▶); Manley et al. (2002 ▶); Zhichkin et al. (2007 ▶); Capdeville et al. (2002 ▶); Ho et al. (2002 ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O₃
M _r = 256.26
Orthorhombic,
a = 7.8063 (10) Å
b = 12.2856 (11) Å
c = 13.1353 (13) Å
V = 1259.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.35 × 0.14 × 0.13 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: none
4741 measured reflections
1364 independent reflections
1243 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.077
S = 1.02
1364 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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/S1600536808002298/at2536sup1.cif

e-64-0o521-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002298/at2536Isup2.hkl

e-64-0o521-Isup2.hkl^{(67.4KB, 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—H1⋯O1ⁱ	0.92 (3)	1.99 (3)	2.849 (2)	155 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

AS gratefully acknowledges a research grant from Quaid-I-Azam University, Islamabad.

supplementary crystallographic information

Comment

The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structure. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), quinazoline-2,4-diones (Makino et al., 2001) and benzodiazepine-2,5-diones (Ho et al., 2002) and 110 kinase inhibitors 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as centroid elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as a peptidomimetic, have been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002). Pyridylmethyl containing benzanilide are vascular endothelial growth factor receptor and tyrosine kinase inhibitor (Manley et al., 2002). Furthermore, benzamides have been reported to have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999)

Geometric parameters of the title compound are in the usual ranges. The dihedral angle between the two aromatic rings is 41.48 (5)°. The nitro group is twisted by 24.7 (3)° out of the plane of the aromatic ring to which it is attached. The molecules crystallize in chains running along the a axis. The molecules in a chain are connected by N—H···O hydrogen bonds.