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

Mehmet Akkurt; Aliasghar Jarrahpour; Malihe Aye; Mustafa Gençaslan; Orhan Büyükgüngör

doi:10.1107/S1600536808032042

. 2008 Oct 9;64(Pt 11):o2087. doi: 10.1107/S1600536808032042

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

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

PMCID: PMC2959688 PMID: 21580952

Abstract

In the title molecule, C₁₅H₁₄N₂O₄, the dihedral angle between the two benzene rings is 29.52 (8)°. The nitro and two methoxy substituents are almost coplanar with their respective benzene rings. The crystal structure is stabilized by intermolecular C—H⋯O interactions.

Related literature

For general background, see: Bey & Vevert (1977 ▶); Bezas & Zervas (1961 ▶); Fleet & Fleming (1969 ▶); Lucas et al. (1960 ▶); Macho et al. (2004 ▶). For a related structure, see: Akkurt et al. (2005 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M _r = 286.28
Monoclinic,
a = 7.9536 (4) Å
b = 8.2258 (3) Å
c = 21.3418 (10) Å
β = 96.125 (4)°
V = 1388.31 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.25 × 0.21 × 0.18 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.975, T _max = 0.982
14598 measured reflections
2880 independent reflections
1797 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.120
S = 0.83
2880 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.12 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: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536808032042/tk2312sup1.cif

e-64-o2087-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032042/tk2312Isup2.hkl

e-64-o2087-Isup2.hkl^{(138.5KB, 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—H8C⋯O1ⁱ	0.96	2.55	3.255 (3)	130
C8—H8C⋯O4ⁱⁱ	0.96	2.56	3.405 (3)	147
C14—H14⋯O2ⁱⁱⁱ	0.93	2.56	3.246 (2)	131

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

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 belong to a widely used group of organic intermediates which are important for production of certain chemicals, such as pharmaceuticals and rubber additives (Macho et al., 2004), and as amino protective groups in organic synthesis (Bey & Vevert, 1977; Lucas et al., 1960; Fleet & Fleming, 1969; Bezas & Zervas, 1961). As we are interested in Schiff bases, we report here the crystal structure of the title compound, (I).

In (I), Fig. 1, the dihedral angle between the two benzene rings (C1–C6) and (C10–C15) is 29.52 (8)° and the C1—N1—C9—C10 torsion angle is 176.12 (15)°. The nitro and two methoxy substituents are coplanar with their respective benzene rings.

The crystal structure of (I) is stabilized by intermolecular C—H···O interactions, Fig. 2 and Table 1.

Experimental

A mixture of 3,4-dimethoxyaniline (3 mmol) and 4-nitrobenzaldehyde (3 mmol) was refluxed in EtOH for 4 h. After cooling the solution, the formed precipitate was filtered off and washed with ethanol to give pure Schiff base as an orange solid in an 89% yield; m. pt. = 429–431 K. IR (KBr, cm^-1): 1600.3 (C?N). ¹H NMR (CDCl₃) δ 3.92, 3.94 (2 x OCH₃, s, 6H), 6.92–8.66 (ArH, m, 7H), 8.90 (HC?N, s, 1H). ¹³C NMR (CDCl₃) δ 55.97, 56.12 (2 OCH₃), 105.63–149.50 (C?C aromatic carbons), 155.03 (C?N).