Crystal structure of (Z)-3-benz­yloxy-6-[(2-hy­droxy­anilino)methyl­idene]cyclo­hexa-2,4-dien-1-one

Nadir Ghichi; Ali Benboudiaf; Hocine Merazig

doi:10.1107/S1600536814024568

. 2014 Nov 26;70(Pt 12):o1292. doi: 10.1107/S1600536814024568

Crystal structure of (Z)-3-benzyloxy-6-[(2-hydroxyanilino)methylidene]cyclohexa-2,4-dien-1-one

Nadir Ghichi ^a,^*, Ali Benboudiaf ^a, Hocine Merazig ^a

PMCID: PMC4257387 PMID: 25553053

Abstract

In the title compound, C₂₀H₁₇NO₃, the methylidenecyclohexa-2,4-dienone moiety is approximately planar [maximum deviation = 0.0615 (10) Å] and is oriented at diherdral angles of 69.60 (7) and 1.69 (9)° to the phenyl and hydroxybenzene rings, respectively. The amino group links with the carbonyl O atom via an intramolecular N—H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, the molecules are linked by O—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯π interactions, forming a three-dimensional supramolecular architecture.

Keywords: crystal structure, pharmaceutical applications, industrial applications, azomethines, hydrophilicity, drug properties, hydrogen bonding, C—H⋯π interactions

Related literature

For pharmaceutical and industrial applications of azomethines, see: Prakash & Adhikari (2011 ▶). For the effect of hydrophilicity on drug properties, see: Lin & Lu (1997 ▶). graphic file with name e-70-o1292-scheme1.jpg

Experimental

Crystal data

C₂₀H₁₇NO₃
M _r = 319.21
Monoclinic,
a = 12.890 (5) Å
b = 8.343 (5) Å
c = 19.908 (5) Å
β = 129.616 (15)°
V = 1649.2 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.03 × 0.02 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer
10996 measured reflections
2845 independent reflections
2019 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.105
S = 1.01
2845 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814024568/xu5827sup1.cif

e-70-o1292-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024568/xu5827Isup2.hkl

e-70-o1292-Isup2.hkl^{(136.8KB, hkl)}

Click here for additional data file.^{(6.3KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814024568/xu5827Isup3.cml

Click here for additional data file.^{(1MB, tif)}

. DOI: 10.1107/S1600536814024568/xu5827fig1.tif

View of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(1.8MB, tif)}

b . DOI: 10.1107/S1600536814024568/xu5827fig2.tif

Partial view along the b axis of the crystal packing of the title compound, showing the hydrogen bonds as dashed lines (see Table 1 for details).

CCDC reference: 1033206

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

Table 1. Hydrogen-bond geometry (, ).

Cg1 is the centroid of the C15C20 ring.

DHA	DH	HA	D A	DHA
N1H01O2	0.94	1.81	2.594(2)	139
O1H3O2ⁱ	0.82	1.75	2.563(3)	170
C13H13O3ⁱⁱ	0.93	2.53	3.309(3)	141
C14H14A Cg1ⁱⁱⁱ	0.97	2.66	3.406(3)	134

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

Acknowledgments

We thank all researchers of the CHEMS Research Unit, University of Constantine 1, Algeria, for their valuable assistance and MESRS (Algeria) for financial support.

supplementary crystallographic information

S1. Comment

Azomethine compounds are extensively incoporated in many pharmaceutical and food industry applications (Prakash & Adhikari, 2011). Elimination of excess drugs from the bloodstream or body is an essential process to protect against potential toxicity. In most cases the more hydrophilic drugs/pharmacophores are the more they are readily excreted by the kidneys in urine (Lin & Lu, 1997). The existence of conjugated double bonds and more hydroxylic groups in bioactive molecules increases not only their hydrophilicity but also the rate of their membrane absorption. Based on such facts we herein report the crystal structure of a potential bioactive hydrophilic azomethine derivative.

A view of the molecular structure of (I) with numbering Scheme is shown in Fig. 1. In the molecule, the methylene-cyclohexa-2,4-dienone moiety is approximately planar [maximum deviation = 0.0615 (10) Å] and its mean plane is oriented with respect to the terminal benzene rings at 69.60 (7) and 1.69 (9)°, respectively. The amino group links with the carbonyl O atom via an intramolecular N—H···O hydrogen bond, forming an S(6) ring motif. In the crystal, the molecules are linked by the intermolecular O—H···O hydrogen bond, weak C—H···O and C—H···π interactions to form the three dimensional supramolecular architecture.

S2. Experimental

A mixture of 2-aminophenol (1 mmol), and 4-(benzyloxy)-2-hydroxybenzaldehyde (1 mmol) was added and heated to form a clear solution. To this a few drops of conc. HCL was added as a catalyst and refluxed for 4 h. After cooling the solution, After stirring at 80°C for 45 min the formed precipitate was filtered off and washed with ice ether and ethyl acetate to give pure Schiff base as an Orange solid in an 35% yield. The crude product was dissolved in ethyl acetate and two spoons of activated charcoal were added. the mixture was filtered and the product was crystallized from an ethyl acetate solution.