N′-[(E)-4-Benz­yloxy-2-hy­droxy­benzyl­idene]benzohydrazide

P R Reshma; M Sithambaresan; M R Prathapachandra Kurup

doi:10.1107/S1600536812036306

. 2012 Aug 25;68(Pt 9):o2785. doi: 10.1107/S1600536812036306

N′-[(E)-4-Benzyloxy-2-hydroxybenzylidene]benzohydrazide

P R Reshma ^a, M Sithambaresan ^b,^*, M R Prathapachandra Kurup ^a

PMCID: PMC3435816 PMID: 22969662

Abstract

The title compound, C₂₁H₁₈N₂O₃, exists in the E conformation with respect to the azomethane C=N double bond. The central benzene ring is almost coplanar with one of the substituent benzene rings [dihedral angle = 1.74 (5)°] and is approximately orthogonal to the other benzene ring of the molecule [dihedral angle = 86.61 (7)°]. An intramolecular O—H⋯N hydrogen bond occurs. The crystal packing is dominated by N—H⋯O hydrogen bonds, which lead to an infinite chain running parallel to [010].

Related literature

For the biological activity of hydrazones, see: Patil et al. (2010 ▶); Zhang et al. (2010 ▶). For the synthesis of related compounds, see: Emmanuel et al. (2011 ▶); Mangalam & Kurup (2011 ▶). For related structures, see: Lin & Sang (2009 ▶); Mohd Lair et al. (2009 ▶).

Experimental

Crystal data

C₂₁H₁₈N₂O₃
M _r = 346.37
Monoclinic,
a = 10.8053 (6) Å
b = 4.8952 (2) Å
c = 16.3601 (10) Å
β = 95.813 (2)°
V = 860.90 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.969, T _max = 0.978
9033 measured reflections
1705 independent reflections
1593 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.082
S = 1.12
1705 reflections
243 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036306/fj2591sup1.cif

e-68-o2785-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036306/fj2591Isup2.hkl

e-68-o2785-Isup2.hkl^{(84KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812036306/fj2591Isup3.cml

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—H2′⋯O3ⁱ	0.85 (1)	2.09 (1)	2.903 (2)	160 (2)
O2—H2′′⋯N1	0.87 (2)	1.79 (2)	2.592 (2)	152 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for providing the single-crystal X-ray diffraction data. PRR thanks the Council of Scientific and Industrial Research, New Delhi, India, for a Junior Research Fellowship.

supplementary crystallographic information

Comment

Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Patil et al., 2010; Zhang et al., 2010). As a continuous work on the hydrazone compounds, a new hydrazone compound, N'-{(E)-[4-(benzyloxy)-2-hydroxyphenyl]methylidene}benzohydrazide, was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.

The compound crystallizes in monoclinic space group P2₁. The molecule adopts an E configuration with respect to C14=N1 bond (Lin & Sang 2009; Mohd Lair et al., 2009) and it exists in amido form with C15=O3 bond length of 1.224 (3) Å which is very close to a formal C=O bond length [1.21 Å]. The aromatic ring C8—C13 is almost coplanar with the ring C16—C21 with dihedral angle of 1.74 (5)° whilst the ring C1—C6 is approximately orthogonal (86.61 (7)°) to the ring C16—C21.

While the intramolecular hydrogen bond O(2)—H(2'')···N(1) increases the rigidity of the molecule, intermolecular N(2)—H(2')···O(3) hydrogen bond (Table 1) links the adjacent molecules forming an infinite one-dimensional supramolecular chain running parallel to the [010] direction in the unit cell (Fig. 2). Benzohydrazone molecules within these chains also interact through very weak π···π interactions with a shortest centroid-centroid distance of 4.8950 (15) Å that not only augment the stronger N—H···O hydrogen bond but also interconnects the infinite chains forming three-dimensional network in the lattice. The parallel arrangement of the molecules along b axis is shown in Fig. 3.

Experimental

The title compound was prepared by adapting a reported procedure (Emmanuel et al., 2011; Mangalam & Kurup, 2011) by refluxing a mixture of methanolic solutions of benzhydrazide (0.136 g,1 mmol) and 4-benzyloxysalicylaldehyde (0.2282 g,1 mmol) for 4 h. The formed crystals were collected, washed with few drops of methanol and dried over P₄O₁₀in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation from its methanolic solution.