1,2-Bis(2-hy­droxy-5-methyl­benzyl­idene)hydrazine

B Saravanan; A Jayamani; N Sengottuvelan; G Chakkaravarthi; V Manivannan

doi:10.1107/S160053681302148X

. 2013 Aug 7;69(Pt 9):o1394–o1395. doi: 10.1107/S160053681302148X

1,2-Bis(2-hydroxy-5-methylbenzylidene)hydrazine

B Saravanan ^a, A Jayamani ^b, N Sengottuvelan ^b, G Chakkaravarthi ^c,^*, V Manivannan ^a,^*

PMCID: PMC3884483 PMID: 24427035

Abstract

The molecular structure of the title compound, C₁₆H₁₆N₂O₂, is stabilized by intramolecular O—H⋯N hydrogen bonds with S(6) graph-set motifs, so that the molecule is almost planar, with a C=N—N=C torsion angle of −179.7 (2)° and a dihedral angle of 1.82 (12)° between the aromatic rings. In the crystal, weak C—H⋯π interactions lead to the formation of a three-dimensional network.

Related literature

For the biological activity of Schiff base ligands, see: Kelley et al. (1995 ▶); Pandeya et al. (1999 ▶); Singh & Dash (1988 ▶); Tarafder et al. (2002 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For related strucutures, see: Chantrapromma et al. (2010 ▶); Fun et al. (2010 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₂
M _r = 268.31
Orthorhombic,
a = 6.0108 (5) Å
b = 7.3394 (5) Å
c = 31.674 (2) Å
V = 1397.32 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.982, T _max = 0.987
5699 measured reflections
2952 independent reflections
1780 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.154
S = 1.02
2952 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302148X/is5296sup1.cif

e-69-o1394-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302148X/is5296Isup2.hkl

e-69-o1394-Isup2.hkl^{(142KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681302148X/is5296Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.82	1.91	2.635 (3)	146
O1—H1⋯N1	0.82	1.93	2.646 (3)	145
C5—H5⋯Cg1ⁱ	0.93	2.84	3.519 (3)	130
C14—H14⋯Cg2ⁱⁱ	0.93	2.85	3.519 (3)	130

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

Acknowledgments

The authors acknowledge the Department of Chemistry, IIT Madras, for the data collection.

supplementary crystallographic information

1. Comment

Schiff base ligands exhibit anti-cancer, anti-fungal, anti-tumour and anti-HIV activities (Pandeya et al., 1999; Singh & Dash, 1988; Kelley et al., 1995; Tarafder et al., 2002). In the molecular structure of the title compound (Fig. 1), the bond distances are within the normal range (Allen et al., 1987) and are comparable with the related structures (Chantrapromma et al., 2010; Fun et al., 2010). In the molecule, two aromatic rings are almost co-planar, with a dihedral angle of 1.82 (12)°. The hydroxy groups form intramolecular O—H···N hydrogen bonds (O1—H1···N1 and O2—H2A···N2; Table 1) with S(6) graph-set motifs (Bernstein et al., 1995). The crystal structure also exhibits weak intermolecular C—H···π (Table 1) interactions which forms a three dimensional network.

2. Experimental

The title compound was synthesized by mixing a solution (1:2 molar ratio) of hydrazine hydrate (0.20 ml, 4 mmol) and 2-hydroxy-5-methylbenzaldehyde (1.08 g, 8 mmol) in ethanol (30 ml). The resulting solution was refluxed for 4 h, yielding (65%) the pale yellow crystalline solid. The resultant solid was filtered off and washed with methanol. Pale Yellow single crystals of the title compound suitable for X-ray structure determination were recrystalized from dimethylformamide by slow evaporation at room temperature over several days.