(2Z,N′E)-N′-[(2-Hy­droxy-1-naphth­yl)methyl­idene]furan-2-carbohydrazonic acid

Rahman Bikas; Hassan Hosseini Monfared; Keyvan Bijanzad; Ahmet Koroglu; Canan Kazak

doi:10.1107/S1600536810027935

. 2010 Jul 21;66(Pt 8):o2073. doi: 10.1107/S1600536810027935

(2Z,N′E)-N′-[(2-Hydroxy-1-naphthyl)methylidene]furan-2-carbohydrazonic acid

Rahman Bikas ^a,^*, Hassan Hosseini Monfared ^a, Keyvan Bijanzad ^b, Ahmet Koroglu ^c, Canan Kazak ^c

PMCID: PMC3007385 PMID: 21588374

Abstract

In the title compound, C₁₆H₁₂N₂O₃, the dihedral angle between the mean planes of the naphthalene ring system and the furan ring is 21.3 (6)°. The molecular structure is stabilized by an intramolecular O—H⋯N hydrogen bond, which generates an S(6) graph-set motif.

Related literature

For historical background to aroylhydrazones, see: Arapov et al. (1987 ▶); Pickart et al. (1983 ▶); Offe et al. (1952 ▶); Nagaraju et al. (2009 ▶); Ghosh et al. (2007 ▶). For related structures, see: Monfared et al. (2010 ▶); Ali et al. (2005 ▶); Qian et al. (2006 ▶); Tarafder et al. (2002 ▶); Prathapachandra Kurup & Bessy Raj (2007 ▶). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₂N₂O₃
M _r = 280.28
Orthorhombic,
a = 9.7427 (8) Å
b = 21.4182 (8) Å
c = 6.445 (2) Å
V = 1344.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.31 × 0.27 × 0.15 mm

Data collection

STOE IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.970, T _max = 0.985
7278 measured reflections
1440 independent reflections
944 reflections with I > 2σ(I)
R _int = 0.097

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.095
S = 1.02
1440 reflections
191 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027935/jj2034sup1.cif

e-66-o2073-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027935/jj2034Isup2.hkl

e-66-o2073-Isup2.hkl^{(69.6KB, 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
O1—H1⋯N1	0.82	1.84	2.565 (5)	146

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Acknowledgments

The authors are grateful to Zanjan University and Ondokuz Mayis University.

supplementary crystallographic information

Comment

Hydrazone ligands derived from the condensation of aliphatic acid hydrazides or aromatic acid hydrazides with aromatic 2-hydroxy carbonyl compounds are important tridentate O, N,O-donor ligands. These compounds, due to their facile keto-enol tautomerization and the availability of several potential donor sites, can coordinate to metals. Furthermore, the possibility of tautomerism makes their study interesting (Ghosh et al., 2007). Hydrazones have wide spread applications in coordination, analytical and bioinorganic chemistry, and display magnetic, electronic, NLO and fluorescent properties in biologically active compounds (Prathapachandra Kurup et al., 2007). They find applications in the treatment of diseases such as anti-tumor, tuberculosis, leprosy and mental disorder (Nagaraju et al., 2009). As part of our studies on the synthesis and characterization of aroylhydrazone derivatives, we report here the crystal structure of C₁₆H₁₂N₂O₃.

In the title compound, C₁₆H₁₂N₂O₃, the dihedral angle between the mean planes of the naphthalene and furan rings is 21.3 (6)° (Fig.1). The angle formed between the menn planes of the naphthalene substituted hydroxy group (C11/C10/C1/O1/H1) and the 2-carbohydrazonic acid furan substituted hydroxy group (N1/N2/C12/O2/H22) is 17.9 (1)°. Bond distances and angles are in normal ranges (Allen et al., 1987). Crystal packing is stabilized by O1—H1···N1 intramolecular hydrogen bonds which form an S₁¹(6) graph-set motif (Bernstein et al., 1995), Etter et al., 1990), (Fig. 2).

Experimental

All reagents were commercially available and used as received. A methanol (10 ml) solution of 2-hydroxy-1-naphtaldehyde (1.5 mmol) was drop-wise added to a methanol solution (10 ml) of 2-furanecarboxylic acid hydrazide (1.5 mmol), and the mixture was refluxed for 3 h. Then the solution was evaporated on a steam bath to 5 cm³ and cooled to room temperature. Yellow precipitates of the title compound were separated and filtered off, washed with 3 ml of cooled methanol and then dried in air. X-ray quality crystals of the title compound were obtained from methanol by slow solvent evaporation. Yield: 82%, mp 197-198 °C.