Crystal structure of ethyl 2-(2-{(1E)-[(E)-2-(2-hy­droxy­benzyl­idene)hydrazin-1-yl­idene]meth­yl}phen­oxy)acetate

Mehmet Akkurt; Joel T Mague; Shaaban K Mohamed; Eman A Ahmed; Mustafa R Albayati

doi:10.1107/S2056989014027273

. 2015 Jan 3;71(Pt 2):o70–o71. doi: 10.1107/S2056989014027273

Crystal structure of ethyl 2-(2-{(1E)-[(E)-2-(2-hydroxybenzylidene)hydrazin-1-ylidene]methyl}phenoxy)acetate

Mehmet Akkurt ^a, Joel T Mague ^b, Shaaban K Mohamed ^c,^d, Eman A Ahmed ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4384580 PMID: 25878876

Abstract

In the title compound, C₁₈H₁₈N₂O₄, the planes of the benzene rings are twisted with respect to each other at 27.25 (7)°. The molecule displays an extended conformation with an intramolecular O—H⋯N hydrogen bond. In the crystal, weak C—H⋯O interactions link the molecules, forming supramolecular chains running along the b-axis direction.

Keywords: crystal structure, Schiff base ligand, hydrogen bonding

Related literature

For a similar structure, see: Mague et al. (2015 ▸). For background to related Schiff base ligands and their biological activity, see: Adsule et al. (2006 ▸); Karthikeyan et al. (2006 ▸); Amimoto & Kawato (2005 ▸); Cohen & Schmidt (1964 ▸). graphic file with name e-71-00o70-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₈N₂O₄
M _r = 326.34
Monoclinic,
a = 17.6846 (4) Å
b = 4.8645 (1) Å
c = 19.2235 (4) Å
β = 107.357 (1)°
V = 1578.43 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.81 mm⁻¹
T = 150 K
0.20 × 0.09 × 0.06 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.90, T _max = 0.95
11331 measured reflections
3063 independent reflections
2538 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.109
S = 1.06
3063 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027273/xu5832sup1.cif

e-71-00o70-sup1.cif^{(371.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027273/xu5832Isup2.hkl

e-71-00o70-Isup2.hkl^{(168.3KB, hkl)}

Click here for additional data file.^{(6.5KB, cml)}

Supporting information file. DOI: 10.1107/S2056989014027273/xu5832Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989014027273/xu5832fig1.tif

Perspective view of the title molecule with 50% probability ellipsoids and showing the atom labeling scheme and the intramolecular O—H⋯N hydrogen bond.

Click here for additional data file.^{(1.2MB, tif)}

b . DOI: 10.1107/S2056989014027273/xu5832fig2.tif

Packing viewed down the b axis showing C—H⋯O interactions as black dotted lines.

CCDC reference: 1039095

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1AN1	0.84	1.85	2.6441(17)	158
C15H15AO4ⁱ	0.99	2.58	3.3568(19)	136
C15H15BO3ⁱⁱ	0.99	2.57	3.440(2)	147

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

Acknowledgments

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Comment

Schiff bases of salicylaldehyde have gained importance from physiological and pharmacological activities point of view (Adsule et al., 2006; Karthikeyan et al., 2006). They also may exhibit thermochromism or photochromism depending on the planarity or nonplanarity, respectively, of the molecule (Amimoto & Kawato, 2005; Cohen & Schmidt, 1964). As part of our research efforts in the area of schiff base ligands we report in this study the synthesis and crystal structure determination of the title compound.

The title molecule is in an extended conformation with the phenyl rings C1–C6 and C9–C14, respectively, making dihedral angles of 7.4 (1)° and 19.8 (1)° with the mean plane of the central C7, N1, N2, C8 unit. The bond lengths and bond angles of the title molecule are normal and are comparable to those reported for a similar structure (Mague et al., 2015).

The former angle is smaller as a result of the intramolecular O1—H1a···N1 hydrogen bond (Table 1). The packing consists of chains of molecules formed by weak C15—H15B···O3 interactions running parallel to the b axis with adjacent pairs of chains associated via C15—H15a···O4 interactions across centers of symmetry (Fig. 2 and Table 1).

S2. Experimental

A mixture of 0.01 mol of 2-hydroxybenzohydrazide and 0.01 mol of ethyl 2-(2-formylphenoxy)acetate in 20 ml of ethanol was heated under reflux for 2 h. The solid product which precipitated from the hot solution was collected by filtration and dried under vacuum. Colourless crystals sufficient for X-ray diffraction were obtained by recrystallization from an ethanol solution. m.p. 428 K, yield 92%.