N′-[(E)-2,3-Dihy­droxy­benzyl­idene]-2-meth­oxy­benzohydrazide

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

doi:10.1107/S1600536812042390

. 2012 Nov 3;68(Pt 12):o3256. doi: 10.1107/S1600536812042390

N′-[(E)-2,3-Dihydroxybenzylidene]-2-methoxybenzohydrazide

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

PMCID: PMC3588810 PMID: 23468775

Abstract

The title compound, C₁₅H₁₄N₂O₄ adopts an E conformation about the azomethine double bond. Intramolecular N—H⋯O and O—H⋯N hydrogen bonds generate S(6) rings and help to establish the molecular conformation. The dihedral angle between the benzene rings is 17.84 (10)°. In the crystal, molecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network with a herring-bone pattern arranged parallel to the bc plane.

Related literature

For applications and the biological activity of Schiff bases, see: Panneerselvam et al. (2009 ▶); Khan et al. (2009 ▶); Jarahpour et al. (2007 ▶). For related structures, see: Baharudin et al. (2012 ▶); Taha et al. (2012 ▶); Promdet et al. (2011 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M _r = 286.28
Orthorhombic,
a = 14.1479 (17) Å
b = 8.6567 (11) Å
c = 22.570 (3) Å
V = 2764.2 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.56 × 0.18 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.945, T _max = 0.996
15288 measured reflections
2574 independent reflections
1658 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.115
S = 1.03
2574 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 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.^{(23.9KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042390/pv2594sup1.cif

e-68-o3256-sup1.cif^{(23.9KB, cif)}

Click here for additional data file.^{(126.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042390/pv2594Isup2.hkl

e-68-o3256-Isup2.hkl^{(126.5KB, hkl)}

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

Supplementary material file. DOI: 10.1107/S1600536812042390/pv2594Isup3.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—H1A⋯O2	0.91 (2)	1.90 (2)	2.608 (2)	133 (2)
O3—H3A⋯O1ⁱ	0.90 (3)	1.75 (3)	2.631 (2)	167 (2)
O4—H4A⋯N2	0.85 (2)	1.89 (2)	2.658 (2)	151 (2)
C8—H8A⋯O3ⁱⁱ	0.93	2.33	3.189 (2)	153

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

supplementary crystallographic information

Comment

Schiff bases represent an important group of organic compounds with a wide range of medicinal applications (Panneerselvam et al., 2009; Khan et al., 2009; Jarahpour et al., 2007). The title Schiff base was synthesize as a part of our ongoing resaerch to study different bioactive organic compounds.

The bond lengths and angle in the title compound (Fig. 1) are similar to the corresponding bond lengths and bond angles reported in structurally realted Schiff bases (Taha et al., 2012; Promdet et al., 2011). The E configuration of azomethine oelfinic bond is stabilized by two intramolecular N1—H1A···O2, O4—H4A···N2 hydrogen bonds. O3—H3A···O1 and C8—H8A···O3 hydrogen bonds play important roles in stabilizing the crystal structure by forming a two-dimensional-network arranged parallel to the bc plane in a zig zag fashion (Table 2 and Fig. 2).

Experimental

The title compound was synthesized by refluxing a mixture of 2-methoxybenzohydrazide (0.332 g, 2 mmol) and 2,3-dihydroxybenzaldehyde (0.276 g, 2 mmol) in methanol (40 ml) along with a catalytical amount of acetic acid for 3 hr. The progress of reaction was monitored by TLC. After completion of reaction, the solvent was evaporated under reduced vacuum to afford crude product which was recrystallized by dissolving in methanol at room temperature to obtain pure needles (0.458 g, 80% yield). All chemicals were purchased by sigma Aldrich Germany.