(E)-N′-(2-Hydr­oxy-4-methoxy­benzyl­idene)isonicotinohydrazide monohydrate

San-Jun Peng; Hai-Yun Hou

doi:10.1107/S1600536808029619

. 2008 Sep 24;64(Pt 10):o1996–o1997. doi: 10.1107/S1600536808029619

(E)-N′-(2-Hydroxy-4-methoxybenzylidene)isonicotinohydrazide monohydrate

San-Jun Peng ^a,^*, Hai-Yun Hou ^b

PMCID: PMC2959424 PMID: 21201195

Abstract

The title compound, C₁₄H₁₃N₃O₃·H₂O, was prepared by the reaction of 4-methoxysalicylaldehyde and isonicotinohydrazide in ethanol. The Schiff base molecule is not planar and has an E configuration with respect to the methylidene unit. The dihedral angle between the benzene and pyridine rings is 36.8 (2)°. In the molecule there is an intramolecular O—H⋯N hydrogen bond involving the hydroxyl substituent and the N atom of the 2-hydroxy-4-methoxybenzylidene unit. In the crystal, the molecules are linked through intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background on the biological properties of hydrazones, see: El-Tabl et al. (2008 ▶); Chen et al. (2008 ▶); Alvarez et al. (2008 ▶); Ventura & Martins (2008 ▶); Kalinowski et al. (2008 ▶). For related structures, see: Peng & Hou (2008 ▶); Shan et al. (2008 ▶); Fun et al. (2008 ▶); Yehye et al. (2008 ▶); Ejsmont et al. (2008 ▶); Han et al. (2006 ▶); Lu et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₃N₃O₃·H₂O
M _r = 289.29
Monoclinic,
a = 7.299 (4) Å
b = 12.537 (6) Å
c = 14.808 (7) Å
β = 96.281 (8)°
V = 1346.9 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 (2) K
0.23 × 0.23 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.976, T _max = 0.977
7804 measured reflections
3041 independent reflections
2129 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.112
S = 1.03
3041 reflections
201 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029619/su2062sup1.cif

e-64-o1996-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029619/su2062Isup2.hkl

e-64-o1996-Isup2.hkl^{(149.2KB, hkl)}

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—H1⋯N1	0.82	1.92	2.644 (2)	146
O4—H4B⋯O2ⁱ	0.853 (9)	2.072 (10)	2.924 (2)	176 (2)
O4—H4A⋯N3ⁱⁱ	0.861 (9)	1.971 (10)	2.832 (2)	178 (2)
N2—H2⋯O4ⁱⁱⁱ	0.903 (9)	2.024 (11)	2.915 (2)	169 (2)

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

Acknowledgments

The corresponding author gratefully acknowledges Changsha University of Science and Technology for research grants.

supplementary crystallographic information

Comment

Hydrazones derived from the reactions of aldehydes with hydrazides show potential biological properties (El-Tabl et al., 2008; Chen et al., 2008; Alvarez et al., 2008; Ventura & Martins, 2008; Kalinowski et al., 2008). In the last few years, a large number of hydrazones have been reported (Peng & Hou, 2008; Shan et al., 2008; Fun et al., 2008; Yehye et al., 2008; Ejsmont et al., 2008). As a continuous study, the crystal structure of the title compound, (I), is reported in this paper.

The molecular structure of compound (I) is illustrated in Fig. 1. It consists of a Schiff base molecule and a water molecule of crystallization. The C7═N1 bond length of 1.276 (2) Å indicates a typical C═N double bond. The Schiff base molecule has an E configuration with respect to the methylidene unit (C7═N1), as observed in similar compounds (Han et al., 2006; Lu et al., 2008). In the molecule there is an intramolecular O-H···N hydrogen bond involving the hydroxyl substituent and the N-atom of the 2-hydroxy-4-methoxybenzylidene moiety (Table 1). The dihedral angle between the benzene and pyridine rings is 36.8 (2)°, indicating the molecule is not planar. The bond lengths are in normal ranges (Allen et al., 1987).

In the crystal structure, symmetry related molecules are linked through intermolecular O—H···O, O—H···N and N—H···O hydrogen bonds (Table 1), forming layers parallel to the bc plane (Fig. 2).

Experimental

4-Methoxysalicylaldehyde (0.152 g, 1 mmol) was dissolved in 95% ethanol (50 ml), then isonicotinohydrazide (0.137 g, 1 mmol) was added slowly to the solution, and the mixture was heated at reflux with continuous stirring for 1 h. The solution was cooled to room temperature, yielding colorless crystallites. Recrystallization from a 95% ethanol yielded block-like single crytals of compound (I).