(E,E)-N′-{4-[(2-Benzoyl­hydrazin-1-yl­idene)meth­yl]benzyl­idene}benzo­hydrazide

Ramin Karimian; Hassan Hosseini-Monfared; Rahman Bikas; N Burcu Arslan; Canan Kazak; Ahmet Koroglu

doi:10.1107/S1600536812014687

. 2012 Apr 18;68(Pt 5):o1433. doi: 10.1107/S1600536812014687

(E,E)-N′-{4-[(2-Benzoylhydrazin-1-ylidene)methyl]benzylidene}benzohydrazide

Ramin Karimian ^a,^‡, Hassan Hosseini-Monfared ^b, Rahman Bikas ^c,^*, N Burcu Arslan ^d, Canan Kazak ^d, Ahmet Koroglu ^d

PMCID: PMC3344553 PMID: 22590315

Abstract

In the title compound, C₂₂H₁₈N₄O₂, the molecules lie across an inversion centre. The dihedral angle between the mean planes of the central and terminal benzene rings is 66.03 (2)°. The molecule displays trans and anti conformations about the C=N and N—N bonds, respectively. In the crystal, N—H⋯O hydrogen bonds, with the O atoms of C=O groups acting as acceptors, link the molecules into a chain along [101].

Related literature

For historical background to aroylhydrazones, see: Savanini et al. (2002 ▶). For related structures, see: Bikas et al. (2012 ▶, 2010a ▶,b ▶); Hosseini Monfared et al. (2010a ▶). For catalytic applications of aroylhydrazones, see: Hosseini Monfared et al. (2010b ▶).

Experimental

Crystal data

C₂₂H₁₈N₄O₂
M _r = 370.40
Monoclinic,
a = 30.569 (3) Å
b = 5.1845 (3) Å
c = 12.5191 (11) Å
β = 112.408 (7)°
V = 1834.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.42 × 0.22 × 0.08 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.976, T _max = 0.992
13265 measured reflections
1905 independent reflections
965 reflections with I > 2σ(I)
R _int = 0.105

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.078
S = 0.94
1905 reflections
163 parameters
All H-atom parameters refined
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.14 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 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014687/qm2059sup1.cif

e-68-o1433-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014687/qm2059Isup2.hkl

e-68-o1433-Isup2.hkl^{(91.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812014687/qm2059Isup3.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
N1—H1⋯O1ⁱ	0.87 (2)	2.19 (2)	3.056 (3)	171 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Islamic Azad University (Tabriz Branch), the University of Zanjan and Ondokuz Mayis University.

supplementary crystallographic information

Comment

The design, synthesis, and characterization of metal complexes with Schiff-base ligands play a vital role in the coordination chemistry of transition metals. Hydrazones are a special group of compounds in the Schiff base family that are characterized by the presence of RR'C=N–N=C(O)R'' which two inter-linked nitrogen atoms (–N—N–) separate them from imines, oximes, etc. Hydrazone ligands derived from the condensation of acid hydrazides (R–CO–NH–NH₂) with aromatic carbonyl compounds are important O, N-donor ligands. As biologically active compounds, hydrazones find application in the treatment of diseases such as tuberculosis, leprosy and mental disorder and also as anti-tumor agents. Hydrazone Schiff bases also have wide spread applications in fields such as coordination chemistry, bioinorganic chemistry , magnetics, electronics, nonlinear optics and fluorescent materials. Aroylhydrazone complexes also seem to be good candidates for catalytic oxidation studies because of their resistance to oxidation (Hosseini Monfared et al., 2010b). As part of our studies on the synthesis and characterization of hydrazone derivatives (Bikas et al., 2012, 2010a,b), we report here the crystal structure of (N',N''E,N',N''E)-N',N''-(1,4-phenylenebis(methan-1-yl-1-ylidene))dibenzohydrazide. The molecules of C₂₂H₁₈N₄O₂, lie across inversion centres and the asymmetric unit contains a half molecule (Fig. 1). The terminal benzene rings are parallel to each other and the distance of two planes which embrace these rings is 3.168 Å apart. The dihedral angle between the mean planes of the central and two terminal benzene rings is 66.03 (2)°. The molecule displays a trans configuration with respect to the C=N and N—N bonds. The packing diagram of the title compound is shown in Fig. 2. There are two strong intermolecular N—H···O hydrogen bonds in which the O atoms of the carbonyl groups (–C=O) act as hydrogen acceptors for the hydrogen of N—H and a one-dimensional chain is formed by these hydrogen bonds (Fig. 3).

Experimental

For preparing the title compound a methanol (10 ml) solution of benzhydrazide (3 mmol) was added drop-wise to a methanol solution (10 ml) of terephthalaldehyde (1.5 mmol), and the mixture was refluxed for 4 h. The solution was then evaporated on a steam bath to 5 cm³ and cooled to room temperature. The white precipitates of the title compound were separated and filtered off, washed with 3 ml of cooled methanol and then dried in air. Colorless crystals were obtained from its methanol solution by thermal gradient method. Yield: 93%. IR (cm^-1): 3253 (s, broad, N—H), 1654 (vs, C=O), 1607 (s, C=N), 1546 (vs), 1507 (m), 1361 (s), 1284 (vs), 1146 (s), 1069 (s), 969 (m), 915 (m), 846 (m), 723 (s), 692 (s), 661 (s), 569 (w), 538 (w), 423 (w).