(E)-N′-(4-Meth­oxy­benzyl­idene)-2-m-tolyl­acetohydrazide

A S Praveen; Jerry P Jasinski; Amanda C Keeley; H S Yathirajan; B Narayana

doi:10.1107/S1600536812047113

. 2012 Nov 24;68(Pt 12):o3435. doi: 10.1107/S1600536812047113

(E)-N′-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide

A S Praveen ^a, Jerry P Jasinski ^b,^*, Amanda C Keeley ^b, H S Yathirajan ^a, B Narayana ^c

PMCID: PMC3589016 PMID: 23476252

Abstract

In the title molecule, C₁₇H₁₈N₂O₂, the benzene rings form a dihedral angle of 83.0 (7)°. In the crystal, N—H⋯O hydrogen bonds, in an R ² ₂(8) graph-set motif, link molecules into centrocymmetric dimers, and weak C—H⋯π interactions further link these dimers into columns in [100].

Related literature

For the biological activity of Schiff bases, see: Desai et al. (2001 ▶); El-Masry et al. (2000 ▶); Hodnett & Dunn (1970 ▶); Pandey et al. (1999 ▶); Singh & Dash (1988 ▶). For Schiff bases employed as ligands for complexation of metal ions, see: Aydogan et al. (2001 ▶). For Schiff bases with applications in dyes and pigments, see: Taggi et al. (2002 ▶). For related structures, see: Akkurt et al. (2011 ▶); Lv et al. (2009a ▶,b ▶); Yu & Lv (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₂
M _r = 282.33
Triclinic,
a = 6.4961 (8) Å
b = 9.8047 (10) Å
c = 12.7464 (13) Å
α = 112.130 (9)°
β = 95.507 (10)°
γ = 96.601 (9)°
V = 738.45 (14) Å³
Z = 2
Cu Kα radiation
μ = 0.68 mm⁻¹
T = 173 K
0.34 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.735, T _max = 1.000
4418 measured reflections
2840 independent reflections
2032 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.158
S = 1.04
2840 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Click here for additional data file.^{(23.6KB, cif)}

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812047113/cv5364sup1.cif

e-68-o3435-sup1.cif^{(23.6KB, cif)}

Click here for additional data file.^{(139.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047113/cv5364Isup2.hkl

e-68-o3435-Isup2.hkl^{(139.4KB, hkl)}

Click here for additional data file.^{(2.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812047113/cv5364Isup3.cml

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

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

Cg is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.04	2.902 (2)	178
C15—H15⋯Cg ⁱⁱ	0.93	2.63	3.557 (2)	173

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

Acknowledgments

ASP thanks UOM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Schiff bases are known to have biological activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh et al., 1988), antitumor (Hodnett et al., 1970; Desai et al., 2001), and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions (Aydogan et al., 2001). On the industrial scale, they have wide range of applications such as dyes and pigments (Taggi et al., 2002). The crystal structures of some Schiff base hydrazines, viz., N'-(2-methoxybenzylidene) acetohydrazide (Yu & Lv, 2010), 2-[6-(4-chlorophenyl)imidazo[2,1-b][1,3] thiazol-2-yl]-N'-[(E)-4-methoxybenzylidene]acetohydrazide (Akkurt et al., 2011), N'-(3-methoxybenzylidene)acetohydrazide and N'-(3,4-dimethoxybenzylidene)acetohydrazide (Lv et al., 2009a,b). In view of the importance of hydrazides, the crystal structure of title compound (I) is reported.

In the title molecule, C₁₇H₁₈N₂O₂, two benzene rings form a dihedral angle of 83.0 (7)° (Fig. 1). Bond lengths are in normal ranges (Allen, 1987). In the crystal, N—H···O hydrogen bonds (Table 1), in an R²₂(8) graph set motif, link molecules into centrocymmetric dimers, and weak C–H···π interactions (Table 1) link further these dimers into columns in [100] (Fig. 2).

Experimental

To a stirred solution of 2-m-tolylacetohydrazide (1 g, 6.09 mmol) in ethanol (10 mL), 4-methoxybenzaldehyde (0.79 g, 6.09 mmol) was added (Fig. 3) and strirred at room temperature for 30 minutes. Precipitated solid was filtered and dried. The single crystal was grown from ethyl acetate by slow evaporation method and yield of the compound was 94% (m.p.: 403-405 K).