3,4-Dimeth­oxy-N-(3-nitro­benzyl­idene)aniline

Mehmet Akkurt; Ali Asghar Jarrahpour; Malihe Aye; Mustafa Gençaslan; Orhan Büyükgüngör

doi:10.1107/S1600536808034193

. 2008 Oct 22;64(Pt 11):o2175–o2176. doi: 10.1107/S1600536808034193

3,4-Dimethoxy-N-(3-nitrobenzylidene)aniline

Mehmet Akkurt ^a,^*, Ali Asghar Jarrahpour ^b, Malihe Aye ^b, Mustafa Gençaslan ^a, Orhan Büyükgüngör ^c

PMCID: PMC2959659 PMID: 21581035

Abstract

The title compound, C₁₅H₁₄N₂O₄, has two crystallographically independent molecules in the asymmetric unit. In both molecules, the nitro and the two methoxy substituents are coplanar with the benzene rings to which they are attached. The benzene rings are nearly coplanar, with dihedral angles between the two benzene rings of 10.39 (8) and 5.95 (8)° in the two molecules. The two independent molecules in the asymmetric unit are rotated with respect to each other such that the dihedral angles between equivalent benzene rings are 49.11 (8) and 63.93 (8)°. In the crystal structure, intermolecular C—H⋯O hydrogen-bond contacts and a weak C—H⋯π interaction are observed.

Related literature

For general background, see: Arora et al. (2002 ▶); Desai et al. (2001 ▶); El-masry et al. (2000 ▶); Jarrahpour & Khalili (2006 ▶); Jarrahpour et al. (2004 ▶); More et al. (2001 ▶); Phatak et al. (2000 ▶); Samadhiya & Halve (2001 ▶); Singh & Dash (1988 ▶); Tanaka & Shiraishi (2000 ▶). For related structures, see: Akkurt et al. (2005 ▶, 2008 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M _r = 286.28
Triclinic,
a = 8.6345 (8) Å
b = 8.6540 (8) Å
c = 19.2304 (17) Å
α = 96.629 (7)°
β = 97.338 (7)°
γ = 102.075 (7)°
V = 1378.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.78 × 0.36 × 0.07 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.925, T _max = 0.993
21166 measured reflections
6330 independent reflections
3703 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.119
S = 0.98
6330 reflections
380 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034193/ez2145sup1.cif

e-64-o2175-sup1.cif^{(32.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034193/ez2145Isup2.hkl

e-64-o2175-Isup2.hkl^{(303.5KB, 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
C8—H8A⋯O7ⁱ	0.96	2.39	3.268 (3)	152
C14—H14⋯O5ⁱⁱ	0.93	2.55	3.206 (2)	128
C22—H22A⋯O1ⁱⁱⁱ	0.96	2.60	3.410 (3)	143
C28—H28⋯O4^iv	0.93	2.57	3.222 (2)	128
C18—H18⋯Cg1	0.93	2.89	3.654 (2)	141

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C10–C15 ring.

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

Schiff bases are widely used for synthetic purposes both by organic and inorganic chemists (Arora et al., 2002) and have uses as biological, analytical, polymer and liquid crystalline materials (Tanaka & Shiraishi, 2000). Schiff bases are reported to show a variety of biological activities such as antibacterial (Jarrahpour & Khalili, 2006; Jarrahpour et al., 2004; El-masry et al., 2000), antifungal (More et al., 2001; Singh & Dash, 1988), anticancer (Desai et al., 2001; Phatak et al., 2000) and herbicidal activities (Samadhiya & Halve, 2001). As an extension of our work on Schiff bases, we report here the crystal structure of the title compound (I).

The two molecules of (I) in the asymetric unit are shown in Fig. 1. In both molecules, the NO₂ and the two –OCH₃ substituents are coplanar with the benzene rings and the dihedral angles between the two benzene rings are 10.39 (8)° for C1–C6 and C10–C15 in molecule 1, and 5.95 (8)° for C16–C21 and C25–C30 in molecule 2. The dihedral angles between tequivalent benzene rings in the two independent molecules in the asymmetric unit are 49.11 (8)° for C1–C6 and C16–C21, and 63.93 (8)° for C10–C15 and C25–C30.

In the crystal structure, the packing is stabilized by intermolecular C—H···O type hydrogen contacts and a weak C—H···π interaction (Table 1 and Fig. 2).

Experimental

A mixture of 3,4-dimethoxyaniline (3 mmol) and 3-nitrobenzaldehyde(3 mmol) was refluxed in EtOH for 4 h. After cooling the solution, the precipitate formed was filtered off and washed with ethanol to give the pure Schiff base as a dark yellow solid [yield 75%, m.p. 389–391 K]. IR(KBr) (cm^-1) 1616.2 (C═N). ¹H-NMR (CDCl₃) δ (p.p.m.) 3.92,3.94 (2 OCH₃, 2 s, 6H), 6.87–8.72 (ArH, m, 7H), 8.89 (HC═N, s, 1H). ¹³C-NMR (CDCl₃) δ (p.p.m.) 55.96, 56.11 (2 OCH₃), 105.62–149.47 (C=C aromatic carbons), 154.97 (C═N).