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

Mei Li; Xin Chen

doi:10.1107/S1600536808036015

. 2008 Nov 8;64(Pt 12):o2291. doi: 10.1107/S1600536808036015

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

Mei Li ^a,^*, Xin Chen ^a

PMCID: PMC2959811 PMID: 21581269

Abstract

In the title compound, C₁₅H₁₃NO₅, the vanillin group makes a dihedral angle of 4.95 (8)° with the benzene ring of the nitrobenzene group. The packing is stabilized by weak, non-classical intermolecular C—H⋯O interactions which link molecules into chains running along the c axis.

Related literature

For general background on Schiff bases, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶);

Experimental

Crystal data

C₁₅H₁₃NO₅
M _r = 287.26
Orthorhombic,
a = 13.743 (3) Å
b = 12.526 (3) Å
c = 16.384 (3) Å
V = 2820.4 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 (2) K
0.23 × 0.18 × 0.12 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
15172 measured reflections
2877 independent reflections
1540 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.132
S = 0.99
2877 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 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, 71007a. DOI: 10.1107/S1600536808036015/at2666sup1.cif

e-64-o2291-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036015/at2666Isup2.hkl

e-64-o2291-Isup2.hkl^{(141.3KB, 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
C14—H14⋯O5ⁱ	0.93	2.60	3.405 (3)	146

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Schiff-base ligands have received a good deal of attention in biology and chemistry (Kahwa et al., 1986). Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). As a part of our interest in the coordination properties of Schiff bases functioning as ligands, we investigated the title compound, (I), used as a precursor in the preparation of Schiff bases.

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The vanillin group (C1—C7/O3/O4) is essentially planar (except the methyl H atoms), with an r.m.s. deviation for fitted atoms of 0.035 (3) Å. This group makes a dihedral angle of 4.95 (8)° with the benzene ring (C10—C15) of the nitrobenzene group.

The crystal packing is stabilized by weak, non-classical intermolecular C14—H14···O5═C7 interactions that link adjacent molecules into one-dimensional chains running along the c axis (Table 1, Fig. 2).

Experimental

An anhydrous acetonitrile solution (100 ml) of 4-hydroxy-3-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, in 30 min., and the mixture refluxed for 24 h under 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, and then dried in a vacuum to give the pure compound in 74% yield. Pale-yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.