4-Meth­oxy-3-(4-nitro­benz­yloxy)benzaldehyde

Zhong-Yu Duan; Guo-Li Ma; Li-Ping Yang

doi:10.1107/S1600536811016618

. 2011 May 11;67(Pt 6):o1377. doi: 10.1107/S1600536811016618

4-Methoxy-3-(4-nitrobenzyloxy)benzaldehyde

Zhong-Yu Duan ^a,^*, Guo-Li Ma ^a, Li-Ping Yang ^a

PMCID: PMC3120527 PMID: 21754767

Abstract

In the title compound, C₁₅H₁₃NO₅, the two benzene rings make a dihedral angle of 3.98 (7)°. The crystal packing is stabilized by weak non-classical intermolecular C—H⋯O interactions that link molecules into centrosymmetric tetramers.

Related literature

For general background to the use of Schiff base derivatives in the development protein and enzyme mimics, see: Santos et al. (2001 ▶). For a closely related crystal structure, see: Li & Chen (2008 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₃NO₅
M _r = 287.26
Monoclinic,
a = 6.853 (1) Å
b = 11.994 (2) Å
c = 16.405 (3) Å
β = 98.28 (3)°
V = 1334.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 294 K
0.22 × 0.16 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.932, T _max = 0.988
10078 measured reflections
3161 independent reflections
2441 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.133
S = 1.12
3161 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 I, global. DOI: 10.1107/S1600536811016618/wn2430sup1.cif

e-67-o1377-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016618/wn2430Isup2.hkl

e-67-o1377-Isup2.hkl^{(155.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016618/wn2430Isup3.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
C12—H12⋯O3ⁱ	0.93	2.42	3.280 (2)	154
C9—H9A⋯O5ⁱⁱ	0.97	2.53	3.383 (2)	147
C8—H8B⋯O4ⁱⁱⁱ	0.96	2.55	3.410 (3)	150

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

Acknowledgments

The project was supported by Hebei Provincial Natural Science Foundation of China (project grant No. B2010000039).

supplementary crystallographic information

Comment

Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). The synthesis and crystal structures of numerous derivatives have been published. In particular, the isomeric 3-methoxy-4-(4-nitrobenzyloxy)benzaldehyde crystal structure has been reported (Li & Chen, 2008). As a part of our interest in the coordination properties of Schiff bases functioning as ligands, we have investigated the title compound, which has been used as a precursor in the preparation of Schiff bases.

In the title molecule (Fig. 1), bond lengths (Allen et al., 1987) and angles are within normal ranges. The two benzene rings make a dihedral angle of 3.98 (7)° with each other. A similar value of 4.99 (6)° is observed in 3-methoxy-4-(4-nitrobenzyloxy)benzaldehyde (Li & Chen, 2008).

The crystal packing is stabilised by weak, non-classical intermolecular C12—H12···O3═C7, C8—H8B···O4 and C9—H9A···O5 interactions that link adjacent molecules into centrosymmetric tetramers (Table 1, Fig. 2).

Experimental

An anhydrous acetonitrile solution (100 ml) of 3-hydroxy-4-methoxybenzaldehyde (1.52 g, 10 mmol) was added dropwise to a solution (50 ml) of 1-(bromomethyl)-4-nitrobenzene (2.16 g, 10 mmol) and pyridine (0.79 g, 10 mmol) in acetonitrile, over a period of 30 min., and the mixture refluxed for 24 h under a nitrogen atmosphere. The solvent was removed and the resultant mixture poured into ice-water (100 ml). The yellow precipitate was then isolated and recrystallized from acetonitrile. It was then dried in a vacuum to give the pure compound in 78% yield. Pale-yellow single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.