(E)-2-(4-Nitro­benzyl­ideneamino)benzamide

Shu-Liang Wang; Ke Yang; Xiang-Shan Wang; Shu-Jiang Tu

doi:10.1107/S160053680902203X

. 2009 Jun 13;65(Pt 7):o1581. doi: 10.1107/S160053680902203X

(E)-2-(4-Nitrobenzylideneamino)benzamide

Shu-Liang Wang ^a,^*, Ke Yang ^a, Xiang-Shan Wang ^a, Shu-Jiang Tu ^a

PMCID: PMC2969303 PMID: 21582857

Abstract

The title compound, C₁₄H₁₁N₃O₃, adopts an E conformation, with a dihedral angle of 41.8 (1) ° between the mean planes of the two benzene rings. One of the amino H atoms forms an intramolecular hydrogen bond with the amide N atom, while the other H atom forms an intermolecular hydrogen bond with the carbonyl O atom of an adjacent molecule, forming dimers about inversion centers. A non-classical intermolecular C—H⋯O hydrogen bond also links adjacent molecules into dimers.

Related literature

For Schiff bases complexes with metal ions, see: Kannan & Ramesh (2006 ▶); Lv et al. (2006 ▶); Maurya et al. (2006 ▶); Parekh et al. (2006 ▶); Vanco et al. (2004 ▶).

Experimental

Crystal data

C₁₄H₁₁N₃O₃
M _r = 269.26
Monoclinic,
a = 7.3863 (2) Å
b = 12.2657 (3) Å
c = 14.1414 (4) Å
β = 97.248 (1)°
V = 1270.95 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.45 × 0.29 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
9505 measured reflections
2278 independent reflections
1809 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.093
S = 1.04
2278 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902203X/pv2166sup1.cif

e-65-o1581-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902203X/pv2166Isup2.hkl

e-65-o1581-Isup2.hkl^{(112KB, 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
C13—H13A⋯O2ⁱ	0.93	2.44	3.1903 (19)	138
N1—H1B⋯O3ⁱⁱ	0.904 (18)	2.059 (19)	2.9581 (17)	173.3 (15)
N1—H1A⋯N2	0.877 (18)	1.999 (18)	2.7027 (18)	136.4 (15)

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

Acknowledgments

We are grateful to the National Natural Science Foundation of China (20802061), the Natural Science Foundation (08KJD150019) and the Qing Lan Project (08QLT001) of Jiangsu Education Committee for financial support.

supplementary crystallographic information

Comment

Schiff bases are well known as ligands for many metal ions, such as copper(II) (Vanco et al., 2005), Vanadium(IV, V) (Maurya et al., 2006) and ruthenium(III) (Kannan & Ramesh, 2006). Some of metal Schiff base complexes possess biological activities. For example, it was reported that oxovanadium(IV) complexes with Schiff bases had antifungal activity (Parekh et al., 2006), cobalt(II) and copper(II) complexes of valine-derived Schiff bases possessed antimicrobial activity (Lv et al., 2006). We have synthesized the title compound, (I), by the reaction of 4-nitrobenzaldehyde, 2-aminobenzamide in an ionic liquid at room temperature which is reported in this article.

The X-ray crystal structure determination indicates that the title compound adopts an E-configuration (Fig. 1). The plane defined as the atoms of C7, C8, C9, N2 and H8A is nearly parallel to the benzene ring (C9—C14), forming a dihedral angle of 0.8 (1)°. The dihedral angle between the basal plane (atoms C7, C8, C9, N2 and H8A) and the other benzene ring (C2—C7) is 41.1 (1)°. the benzene rings make a dihedral angle of 41.8 (1)°.

The classical (N—H···O) and unclassical (C—H···O) hydrogen bonds are present in the crystal structure of (I) (Table 1). One of the hydrogen atoms (H1A) on the amino group forms an intra-molecular hydrogen bond (N1—H1A···N2) with the atom N2, while the other hydrogen atom (H1B) forms an inter-molecular hydrogen bond of the type N—H···O with the atom O3 in the adjacent molecule, forming dimmers. An unclassical intermolecular hydrogen bond (C13—H13A···O2) also links the adjacent molecules into dimmers (Fig. 2). The above inter-molecular hydrogen bonds link the molecules into polymers.

Experimental

The title compound, (I), was prepared by the reaction of 4-nitrobenzaldehyde (2 mmol, 0.302 g) and 2-aminobenzamide (2 mmol, 0.272 g) in an ionic liquid of [Bmim]Br (Bmim = 1-butyl-3-methylimidazolium) (2 ml) at 353 K; m.p. 457–458 K. The single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.