(E)-4-Hy­droxy-N′-(2-meth­oxy­benzyl­idene)benzohydrazide

Hesham Hussein Rassem; Abdussalam Salhin; Baharuddin Bin Salleh; Mohd Mustaqim Rosli; Hoong-Kun Fun

doi:10.1107/S1600536812021952

. 2012 May 23;68(Pt 6):o1832. doi: 10.1107/S1600536812021952

(E)-4-Hydroxy-N′-(2-methoxybenzylidene)benzohydrazide

Hesham Hussein Rassem ^a, Abdussalam Salhin ^a,^‡, Baharuddin Bin Salleh ^b, Mohd Mustaqim Rosli ^c, Hoong-Kun Fun ^c,^*,^§

PMCID: PMC3379405 PMID: 22719603

Abstract

In the title compound, C₁₅H₁₄N₂O₃, the dihedral angle between the benzene rings is 66.56 (5)°. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O interactions link the molecules into a three-dimensional network. A π–π interaction, with a centroid–centroid distance of 3.628 (6) Å, helps to establish the packing.

Related literature

For the properties of hydrazone derivatives, see: Lever (1972 ▶); Pelizzi & Pelizzi (1980 ▶). For related structures, see: Shan et al. (2003 ▶); Fun et al. (1996 ▶); Ferguson et al. (2005 ▶). graphic file with name e-68-o1832-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M _r = 270.28
Orthorhombic,
a = 14.3951 (3) Å
b = 8.7449 (2) Å
c = 21.1047 (4) Å
V = 2656.74 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.49 × 0.28 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.954, T _max = 0.991
32112 measured reflections
4442 independent reflections
3512 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.114
S = 1.03
4442 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021952/hb6791sup1.cif

e-68-o1832-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021952/hb6791Isup2.hkl

e-68-o1832-Isup2.hkl^{(217.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812021952/hb6791Isup3.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—H1N1⋯O2ⁱ	0.916 (16)	2.009 (16)	2.9202 (12)	172.8 (15)
O1—H1O1⋯O2ⁱⁱ	0.87 (2)	1.80 (2)	2.6528 (11)	164.2 (17)
C13—H13A⋯O1ⁱⁱⁱ	0.95	2.52	3.4669 (15)	171

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

Acknowledgments

We thank Universiti Sains Malaysia for awarding an RU (1001/PKIMIA/811196) grant. HKF thank USM for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

The chemical properties of hydrazone derivatives have been intensively investigated in several research fields mainly due to their facile synthesis, tuneable electronic and steric properties, and good chelating ability (Pelizzi & Pelizzi, 1980). Some derivatives of the title compound, (I), were used for the determination of glucose (Lever, 1972). These compounds crystallize in the E conformation (Shan et al., 2003; Fun et al., 1996) and isomeric compounds have also been prepared (Ferguson et al., 2005).

All parameters in (I), are within normal ranges. The dihedral angle between C1—C6 and C9 C14 benzene ring is 66.56 (5)°. In the crystal structure, the molecules are interconnected by N1—H1N1···O2ⁱ, O1—H1O1···O2ⁱⁱ and C13—H13A···O1ⁱⁱⁱ hydrogen bonds. A π—π interaction with centroid-centroid distance of 3.628 (6) Å also occurs (Cg1 = C9—C14, -x, -y, -z).

Experimental

A solution of 2-methoxybenzaldehyde (136 mg, 1 mmol) in methanol (10 ml) was added dropwise to a methanolic solution (10 ml) of 4-hydroxybenzhydrazide (152 mg, 1 mmol) and the mixture was refluxed for 2 h. The resulting solution was condensed on a steam bath to 5 ml and cooled to room temperature. Yellow plates were separated out, washed with cooled methanol and dried in air.