2-Methyl-3-nitro-N-{(E)-[5-(4-nitro­phen­yl)furan-2-yl]methyl­idene}aniline

Merve Pekdemir; Şamil Işık; Sümeyye Gümüş; Erbil Ağar; Sema Öztürk Yıldırım; Ray J Butcher

doi:10.1107/S1600536812033818

. 2012 Aug 4;68(Pt 9):o2630. doi: 10.1107/S1600536812033818

2-Methyl-3-nitro-N-{(E)-[5-(4-nitrophenyl)furan-2-yl]methylidene}aniline

Merve Pekdemir ^a,^*, Şamil Işık ^b, Sümeyye Gümüş ^c, Erbil Ağar ^c, Sema Öztürk Yıldırım ^d,^e, Ray J Butcher ^e

PMCID: PMC3435658 PMID: 22969531

Abstract

In the title Schiff-base type compound, C₁₈H₁₃N₃O₅, the central furan ring makes dihedral angles of 12.80 (7) and 51.43 (4)° with the terminal benzene rings. The dihedral angle between the benzene rings is 45.43 (3)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into layers parallel to (010). In addition, there are π–π stacking interactions within the layer [centroid–centroid distance = 3.584 (1) Å] and between the layers [centroid–centroid distance 3.751 (1) Å].

Related literature

For similar Schiff bases, see: Yamada et al. (2002 ▶); Cukurovali et al. (2002 ▶); Isloor et al. (2009 ▶); Abu Thaher et al. (2012 ▶). For the biological activity of Schiff bases, see: Vijesh et al. (2010 ▶); Tarafder et al. (2002 ▶); Ghorab et al. (2010 ▶); Ali et al. (2002 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₈H₁₃N₃O₅
M _r = 351.31
Monoclinic,
a = 10.9026 (3) Å
b = 10.2798 (3) Å
c = 14.2962 (3) Å
β = 101.529 (2)°
V = 1569.94 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.93 mm⁻¹
T = 123 K
0.50 × 0.40 × 0.40 mm

Data collection

Oxford Diffraction Gemini-R diffractometer
Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2007 ▶), and Clark & Reid (1995 ▶)] T _min = 0.671, T _max = 0.688
6460 measured reflections
3171 independent reflections
2764 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.118
S = 1.05
3171 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812033818/gk2492sup1.cif

e-68-o2630-sup1.cif^{(26.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033818/gk2492Isup2.hkl

e-68-o2630-Isup2.hkl^{(155.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812033818/gk2492Isup3.cml

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
C3—H3A⋯O5ⁱ	0.93	2.58	3.4895 (19)	165
C13—H13A⋯O1ⁱⁱ	0.93	2.53	3.432 (2)	162
C14—H14A⋯O2ⁱⁱⁱ	0.93	2.55	3.361 (2)	147

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

Acknowledgments

RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

supplementary crystallographic information

Comment

Schiff bases have been very important as ligands in the area of coordination chemistry. These ligands and their metal complexes have shown important activity in the field of biology in the past years. Several new examples have been tested for their antitumor, antimicrobial, anticancer and antibacterial activities (Ali et al., 2002; Ghorab et al., 2010; Tarafder et al., 2002; Vijesh et al., 2010). In view of these facts, the aim of this present study is to obtain a structure of the Schiff base, 2-methyl-3-nitro-N-{(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneaniline.

In the title compound (Fig 1), the molecule presents an E configuration with the 2-(4-nitrophenyl)furan group opposite to 1-methyl-2-nitrobenzene group about the N2 ═C11 double bond. This N2 ═C11 double bond distance [1.2783 (19) Å] is longer than the N ═C typical bond distance (Allen et al., 1987), probably due to π conjugation along all the molecule. The torsion angle is 171.79 (14) ° formed by C10—C11—N2—C12. All other bond lengths and angles are within normal ranges (Allen et al., 1987). The central furan ring (C7—C10/O3) is planar, with an r.m.s. deviation for fitted atoms of 0.0019 Å. This plane makes dihedral angles of 12.80 (7) and 51.43 (4) ° with the terminal benzene rings C1—C6 and C12—C17, respectively. The dihedral angle between the two benzene ring is 45.43 (3)°.

In the crystal, C—H···O intermolecular interactions are observed (Table 1) as well as π–π stacking interactions [Cg1···Cg3 (-x,1 - y,-z) = 3.584 (1) Å and Cg3···Cg3 (x, 1 + y, z) = 3.751 (1) Å, where Cg1(O3/C7—C10) and Cg3(C12—C17) are the centroids of the furan and benzene ring, respectively] (Fig. 2).

Experimental

The title compound was prepared by refluxing a mixture containing 5-(4-nitrophenyl)furan-2 carbaldehyde (0.011 g 0.051 mmol) and 2-methyl-3-nitroaniline (0.0077 g 0.051 mmol) in 40 ml of ethanol. The reaction mixture was stirred for 1 h under reflux. The crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation (yield 62%; m.p: 471–474 K).