2-{[2-(2-Hy­droxy-3-meth­oxy­benzyl­idene)hydrazin-1-yl­idene]meth­yl}-6-meth­oxy­phenol

Rong Lu; Wenxia Wang; Xingqiang Lü; Shunsheng Zhao

doi:10.1107/S1600536811036816

. 2011 Sep 30;67(Pt 10):o2702. doi: 10.1107/S1600536811036816

2-{[2-(2-Hydroxy-3-methoxybenzylidene)hydrazin-1-ylidene]methyl}-6-methoxyphenol

Rong Lu ^a,^*, Wenxia Wang ^a, Xingqiang Lü ^a, Shunsheng Zhao ^b

PMCID: PMC3201493 PMID: 22064826

Abstract

The title compound, C₁₆H₁₆N₂O₄, was obtained from the reaction of hydrazine hydrate and o-vanilin in absolute ethanol. The molecule is almost planar (except for the methyl H atoms), with a mean deviation from the plane of 0.0259 Å. The molecular structure also exhibits an approximate non-crystallographic twofold axis. Intramolecular O—H⋯N hydrogen bonds occur. In the crystal, intermolecular C—H⋯O hydrogen bonds generate molecular zigzag sheets. The sheets stack through C—H⋯π interactions, leading to a three-dimensional-network.

Related literature

For the properties and applications of the title compound or similar structural compounds and their metal complexes, see: Lin et al. (2009 ▶); Davidson et al. (2006 ▶); Lin & Zeng (2006 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₄
M _r = 300.31
Monoclinic,
a = 6.3095 (14) Å
b = 17.405 (4) Å
c = 13.606 (3) Å
β = 95.590 (4)°
V = 1487.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.858, T _max = 1.000
7393 measured reflections
2648 independent reflections
1133 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.186
S = 1.07
2648 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811036816/fl2353sup1.cif

e-67-o2702-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036816/fl2353Isup2.hkl

e-67-o2702-Isup2.hkl^{(130.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036816/fl2353Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C2–C7 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2	0.91 (5)	1.82 (5)	2.640 (4)	149 (4)
O2—H2A⋯N1	0.88 (4)	1.82 (4)	2.636 (4)	153 (4)
C16—H16A⋯O4ⁱ	0.96	2.55	3.279 (5)	133
C7—H7A⋯Cg2ⁱⁱ	0.93	2.90	3.694 (4)	144
C13—H13A⋯Cg1ⁱⁱⁱ	0.93	2.89	3.717 (4)	149

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

Acknowledgments

This project was supported by the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2010JM2006, 2011JQ2011) and the Scientific Research Program funded by Shaanxi Provincial Education Department (Program No. 2008 J K440).

supplementary crystallographic information

Comment

The title compound, (I) (Fig. 1), with various chelating atoms, could coordinate with many transition metals (Davidson et al., 2006) and lanthanides (Lin and Zeng, 2006; Lin et al. , 2009) to form functional complexes. The molecule crystallizes in the monoclinic space group P21/c and appears to be almost completely planar (except for the methyl hydrogen atoms) with a mean deviation from the plane ooff 0.0259 Å. The molecule also exhibits a non-crystallographic 2-fold axis. There are intramolecular O—H···N hydrogen bonds, intermolecular C—H···O hydrogen bonds and C—H···π hydrogen bonds. Molecules are linked by the C—H···O hydrogen bonds, generating molecular zigzag sheets, as shown in Fig. 2. The C—H···π hydrogen bonds and stacking interaction of these sheets leads to a three-dimensional-network. (Fig. 3).

Experimental

The title compound was obtained from the reaction of hydrazine hydrate and o-vanilin in absolute ethanol. Hydrazine hydrate (500 mg, 10 mmol) was added to a solution of o-vanilin (3.04 g, 20 mmol) in absolute ethanol (200 ml) and heated to reflux for 2 h. The resulting solution was allowed to evaporate at rt to give a yellow crystal, which was collected by filtration and dried under vacumn;; yield 89.3%. The single-crystal of the title compound suitble for X-ray diffraction was obtained by recrystalization from absolute ethanol.