4-[(2E)-2-(2-Hy­droxy­benzyl­idene)hydrazin-1-yl]benzonitrile

Shaaban K Mohamed; Goran A Bogdanović; Antar A Abdelhamid; Sladjana B Novaković; Herman Potgeiter

doi:10.1107/S1600536812037841

. 2012 Sep 8;68(Pt 10):o2886–o2887. doi: 10.1107/S1600536812037841

4-[(2E)-2-(2-Hydroxybenzylidene)hydrazin-1-yl]benzonitrile

Shaaban K Mohamed ^a,^*, Goran A Bogdanović ^b, Antar A Abdelhamid ^a, Sladjana B Novaković ^b, Herman Potgeiter ^c

PMCID: PMC3470239 PMID: 23125683

Abstract

The asymmetric unit of the title Schiff base, C₁₄H₁₁N₃O, contains two independent molecules which have similar conformations. The dihedral angles between the benzene rings are 4.19 (9) and 14.18 (9)° in the two molecules. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation of each molecules. The crystal packing is dominated by pairs of equivalent N—H⋯N and C—H⋯O hydrogen bonds which arrange the molecules into layers parallel to (-111).

Related literature

For azomethines, see: Archibald et al. (1994 ▶); Harada et al. (1999 ▶); Ogawa et al. (1998 ▶). For the biological properties of Schiff bases, see: Lozier et al. (1975 ▶); Dao et al. (2000 ▶). For their coordination chemistry, see: Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For the structure of related Schiff bases reported by our group, see: Mohamed, Abdelhamid et al. (2012 ▶); Mohamed, Akkurt et al. (2012 ▶). graphic file with name e-68-o2886-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₁N₃O
M _r = 237.26
Triclinic,
a = 8.1917 (7) Å
b = 11.6406 (7) Å
c = 13.4445 (8) Å
α = 103.006 (5)°
β = 104.387 (6)°
γ = 96.426 (6)°
V = 1190.67 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 293 K
0.26 × 0.15 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.827, T _max = 1.000
7913 measured reflections
4592 independent reflections
3696 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.121
S = 1.05
4592 reflections
341 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶)’; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037841/rz2800sup1.cif

e-68-o2886-sup1.cif^{(28.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037841/rz2800Isup2.hkl

e-68-o2886-Isup2.hkl^{(220.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812037841/rz2800Isup3.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
O1A—H1OA⋯N1A	0.98 (2)	1.77 (2)	2.654 (2)	149 (2)
O1B—H1OB⋯N1B	0.90 (2)	1.86 (2)	2.653 (2)	147 (2)
N2A—H1NA⋯N3B ⁱ	0.91 (2)	2.17 (2)	3.065 (2)	166 (2)
N2B—H1NB⋯N3A ⁱⁱ	0.89 (2)	2.25 (2)	3.098 (2)	158 (2)
C7A—H7A⋯O1B ⁱⁱⁱ	0.93	2.55	3.427 (2)	156
C7B—H7B⋯O1A ^iv	0.93	2.49	3.413 (2)	172

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

Acknowledgments

We thank Manchester Metropolitan University for providing X-ray analysis and data refinement facilities. SBN and GAB thank the Ministry of Education, Science and Technological Development of the Republic of Serbia for financial support (projects 172014 and 172035).

supplementary crystallographic information

Comment

Schiff bases have received much attention in recent years (Ogawa et al., 1998; Archibald et al., 1994; Harada et al., 1999) due to their various biological activities and metal chelating properties. In many cases, they were shown to have antibacterial, anticancer, anti- inflammatory and antitoxic properties (Lozier et al., 1975; Dao et al., 2000) and have also been used as versatile ligands in coordination chemistry (Kargar et al., 2009; Yeap et al., 2009). Recently, we reported on the crystal structures of two new Schiff bases (Mohamed, Abdelhamid et al., 2012; Mohamed, Akkurt et al., 2012). As a further investigation of the structures of Schiff base compounds, herin we report the synthesis and crystal structure of the title compound (I) which was obtained unintentionally from the component reaction of cyclohexan-1,3-dione, salicylaldehyde and 4- hydrazinylbenzonitrile in ethanol.

The title compound crystallizes with two independent molecules (A and B) in the asymmetric unit, Fig. 1. The molecules A and B have similar conformation and approximately planar form. In molecules A and B the dihedral angle between the corresponding aromatic rings is 4.19 (9) and 14.18 (9)°, respectively. The torsion angles C8—N2—N1—C1 and N2—N1—C1—C2, within the fragment which connects the rings, are 179.44 (14)/-179.93 (13) and 175.41 (13)/177.44 (12)°, in molecules A and B respectively. All these parameters suggest a somewhat higher planarity of molecule A in comparison to molecule B. The molecules of each type are stabilized by the cyclic intramolecular O1—H1o···N1 hydrogen bond (Table 1). In the crystal packing the A and B molecules mutually interact by the pairs of the strongest N2—H1n···N3 hydrogen bonds (Table 1) which engage the hydrazine donor and the nitirile acceptor from each type of molecule. The chains consisting of A and B molecules further interact by another pair of equivalent C7—H7···O1 interactions to give two dimensional lyres (Fig 2). The interaction between the parallel lyres towards the three-dimensional crystal packing is mostly based on weak van der Waals interactions.

Experimental

The title compound was prepared unintentionally as a major product from reaction of 112 mg (1 mmol) cyclohexane-1,3-dione, 133 mg (1 mmol) 4-hydrazinylbenzonitrile and 122 mg (1 mmol) salicylaldehyde in 50 ml ethanol. The reaction mixture was refluxed for 5 h. The excess solvent was evaporated under vacuum and the residual resins was triturated with cold acetone. The obtained solid was collected by filtration, dried and washed with acetone. Single crystals suitable for X-ray diffraction were grown from acetone solution of (I) using the slow evaporation method. M. p. 469 K.