N′-[(E)-2-Hy­droxy-5-meth­oxy­benzyl­idene]-2-meth­oxy­benzohydrazide

M Syukri Baharudin; Muhammad Taha; Nor Hadiani Ismail; Syed Adnan Ali Shah; Sammer Yousuf

doi:10.1107/S1600536812042389

. 2012 Nov 3;68(Pt 12):o3255. doi: 10.1107/S1600536812042389

N′-[(E)-2-Hydroxy-5-methoxybenzylidene]-2-methoxybenzohydrazide

M Syukri Baharudin ^a, Muhammad Taha ^a, Nor Hadiani Ismail ^b, Syed Adnan Ali Shah ^a,^c, Sammer Yousuf ^d,^*

PMCID: PMC3588809 PMID: 23468774

Abstract

The molecule of the title compound, C₁₆H₁₆N₂O₄, adopts an E conformation about the azomethine C=N double bond. The dihedral angle formed by the benzene rings is 18.88 (9)°. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, which forms an S(6) ring. In the crystal, the molecules are linked into chains parallel to [001] by N—H⋯O hydrogen bonds. The chains are further connected into a three-dimensional network by π–π stacking interactions with centroid–centroid distances of 3.6538 (10) and 3.8995 (11) Å.

Related literature

For the applications and biological activity of Schiff bases, see: Panneerselvam et al. (2009 ▶); Khan et al. (2009 ▶); Jarahpour et al. (2007 ▶); Pandeya et al. (1999 ▶). For related structures, see: Taha et al. (2012a ▶,b ▶); Lu et al. (2008 ▶). graphic file with name e-68-o3255-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₆N₂O₄
M _r = 300.31
Monoclinic,
a = 14.5775 (13) Å
b = 11.0798 (11) Å
c = 9.5893 (9) Å
β = 99.872 (2)°
V = 1525.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.59 × 0.45 × 0.39 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.946, T _max = 0.964
8886 measured reflections
2767 independent reflections
2210 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.124
S = 1.04
2767 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(19.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042389/rz5014sup1.cif

e-68-o3255-sup1.cif^{(19.3KB, cif)}

Click here for additional data file.^{(135.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042389/rz5014Isup2.hkl

e-68-o3255-Isup2.hkl^{(135.9KB, hkl)}

Click here for additional data file.^{(6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812042389/rz5014Isup3.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
O1—H1A⋯N1	0.83 (2)	1.87 (2)	2.605 (2)	146.0 (19)
N2—H2A⋯O3ⁱ	0.835 (17)	2.051 (17)	2.8258 (17)	154.2 (15)

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Applications of Schiff bases are reported in different fields of chemistry with a broad range of biological activities (Panneerselvam et al., 2009, Khan et al., 2009, Jarahpour et al., 2007, Pandeya et al., 1999). The title compound is a Schiff base synthesize as a part of our ongoing resaerch to study different biological activities of this medicinally important class of organic compounds.

The structure of title compound (Fig. 1) is similar to that of the previously published compound N'-(2-hydroxybenzylidene)-2-methoxybenzohydrazide monohydrate (Lu et al., 2008), with the difference that the 2-hydroxy benzene ring is replaced by a 2-hydroxy-5-methoxy phenyl ring (C1–C6). The phenyl rings (C1–C6 and C9–C14) form an angle of 18.88 (9)°. Bond lengths and angles are similar to those observed in structurally related benzohydrazide derivatives (Taha et al., 2012; Lu et al., 2008). The E configuration of the azomethine olefinic bond is stabilized by an intramolecular O1—H1A···N1 hydrogen bond (Table 1) forming a ring of S(6) graph set motif. The crystal structure is stabilized by an intermolecular N2—H2A···O3 interaction forming chains running parallel to the [001] direction (Fig. 2). The chains are further linked into a three-dimensional network by π···π stacking interactions with centroid–centroid distances of 3.6538 (10) and 3.8995 (11) Å.

Experimental

The title compound was synthesized by refluxing a mixture of 2-methoxybenzohydrazide (0.332 g, 2 mmol) and 2-hydroxy-5-methoxybenzaldehyde (0.304 g, 2 mmol) in methanol along with a catalytical amount of acetic acid for 3 hrs. The progress of reaction was monitored by TLC. After completion of reaction, the solvent was evaporated by vacuum to afford the crude product which was recrystallized by dissolving in methanol at room temperature to obtained needle-like crystals (0.504 g, 84% yield). All chemicals were purchased by Sigma Aldrich Germany.