(E)-N′-[1-(2-Hy­droxy­phen­yl)ethyl­idene]-2-phen­oxy­acetohydrazide–2,2′-(1,1′-azinodiethyl­idyne)diphenol (2/1)

Yan-Ru Tang

doi:10.1107/S1600536811023956

. 2011 Jun 25;67(Pt 7):o1819. doi: 10.1107/S1600536811023956

(E)-N′-[1-(2-Hydroxyphenyl)ethylidene]-2-phenoxyacetohydrazide–2,2′-(1,1′-azinodiethylidyne)diphenol (2/1)

Yan-Ru Tang ^a,^*

PMCID: PMC3151930 PMID: 21837188

Abstract

The formula unit of the title molecular complex, 2C₁₆H₁₆N₂O₃·C₁₆H₁₆N₂O₂, consists of two (E)-N′-[1-(2-hydroxyphenyl)ethylidene]-2-phenoxyacetohydrazide molecules and one molecule of 2,2′-(1,1′-azinodiethylidyne)diphenol, with the latter located on a crystallographic inversion center. The acetohydrazide molecules are linked into a supermolecular chain along the c axis by intermolecular N—H⋯O hydrogen bonds. There are also intramolecular O—H⋯N hydrogen bonds in both the acetohydrazide and diphenol molecules.

Related literature

For chemically related applications arising from Schiff base compounds, see: Guo et al. (2010 ▶); Yu et al. (2010 ▶). For related structures, see: Lu et al. (1993 ▶); Matoga et al. (2007 ▶); Tai et al. (2008 ▶); Tan (2009 ▶); Wen et al. (2005 ▶).

Experimental

Crystal data

2C₁₆H₁₆N₂O₃·C₁₆H₁₆N₂O₂
M _r = 836.92
Monoclinic,
a = 12.416 (5) Å
b = 19.322 (6) Å
c = 9.225 (4) Å
β = 106.156 (16)°
V = 2125.8 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.18 × 0.15 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.984, T _max = 0.988
20592 measured reflections
4828 independent reflections
2586 reflections with I > 2σ(I)
R _int = 0.072

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.156
S = 1.03
4828 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023956/ld2015sup1.cif

e-67-o1819-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023956/ld2015Isup2.hkl

e-67-o1819-Isup2.hkl^{(236.5KB, 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
N2—H2A⋯O2ⁱ	0.86	2.14	2.860 (3)	141
O1—H01A⋯N1	0.96	1.63	2.530 (3)	154
O4—H04A⋯N3	1.06	1.58	2.542 (3)	148

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author thanks Changchun Normal University for financial support.

supplementary crystallographic information

Comment

Among the richness of coordination chemistry, acylhydrazone ligands (Yu et al., 2010) have attracted an intense interest due to their potential for magnetochemistry (Guo et al., 2010). Recently, a large number of acylhydrazone derivatives have been prepared (Matoga et al., 2007; Tan, 2009). As a contribution to this field, the isolation and the structure of the title 2/1 co-crystal are presented here .

The molecular structure of 2C₁₆H₁₆N₂O₃.C₁₆H₁₆N₂O₂, together with the atom-numbering scheme, is illustrated in Fig.1. Selected bond lengths and angles are given in Table 1. The asymmetric unit of the title co-crystal comprises two (E)-N'-(1-(2-hydroxyphenyl)ethylidene)-2-phenoxyacetohydrazide (A) molecules and a molecule of 2,2'-(1,1'-Azinodiethylidyne)diphenol (B), with no proton transfer. The 2,2'-(1,1'-Azinodiethylidyne)diphenol molecule (B) has been reported previously (Tai et al., 2008). The N3—N3A (1.394 (4) Å) distance is similar to the corresponding distances observed for other compounds (Lu et al., 1993). In the molecule A, the N1—N2(hydrazine) bond distance of 1.375 (2) Å is shorter than the corresponding N—N value of 1.382 (2) Å in a related compound (Wen et al., 2005). The dihedral angle between both aromatic rings for molecule A is 85.76 (2)°, and the molecules A are linked into supermolecule chain along the c axis by intermolecular N2—H2A···O2I hydrogen bonds [symmetry code: (I) x, 1/2 - y, -1/2 + z] (Fig. 2). In addition, there are intramolecular O1—H01A···N1 and O4—H04A···N3 hydrogen bonds in molecules A and B respectively. Stacking interactions between A and B are within van der Waals contacts (Fig.3).

Experimental

A solution of 2,2'-(1,1'-azinodiethylidyne)diphenol (0.2 mmol) in 10 ml of EtOH was added to a solution of (E)-N'-(1-(2-hydroxyphenyl)ethylidene) -2-phenoxyacetohydrazide (0.2 mmol) in 10 ml of the same solvent, upon which the solution was refluxed for 1 h. Then the yellow solution was obtained after filtering. Two week later, yellow crystals of the title compound were isolated from the solution.