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

Feng Zhi; Rong Wang

doi:10.1107/S1600536810010020

. 2010 Mar 20;66(Pt 4):o892. doi: 10.1107/S1600536810010020

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

Feng Zhi ^a,^*, Rong Wang ^a

PMCID: PMC2984034 PMID: 21580709

Abstract

The title compound, C₁₄H₁₃N₃O₃, was synthesized by the condensation reaction of 2-hydroxy-4-methoxybenzaldehyde with isonicotinohydrazide in a methanol solution. The molecule of the compound displays a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the benzene and the pyridine rings is 27.3 (2)°. In the crystal, molecules are linked by N—H⋯N interactions into zigzag chains with graph-set notation C(7) along [010]. An intramolecular O—H⋯N hydrogen bond is observed.

Related literature

For Schiff base compounds, see: Fan et al. (2007 ▶); Kim et al. (2005 ▶); Nimitsiriwat et al. (2004 ▶). For their biological activity, see: Chen et al. (1997 ▶); Ren et al. (2002 ▶). For related structures, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Yang (2008 ▶); Zhi (2008 ▶, 2009 ▶); Zhi & Yang (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₃N₃O₃
M _r = 271.27
Monoclinic,
a = 8.4704 (11) Å
b = 10.6866 (15) Å
c = 14.848 (2) Å
β = 104.929 (5)°
V = 1298.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.983, T _max = 0.985
7591 measured reflections
2814 independent reflections
2148 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.107
S = 1.05
2814 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010020/bx2271sup1.cif

e-66-0o892-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010020/bx2271Isup2.hkl

e-66-0o892-Isup2.hkl^{(138.2KB, 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
N2—H2⋯N3ⁱ	0.90 (1)	2.22 (1)	3.1000 (17)	169 (2)
O1—H1⋯N1	0.82	1.85	2.5720 (15)	146

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Third Affiliated Hospital of Suzhou University is acknowledged.

supplementary crystallographic information

Comment

Considerable interest has been focused on the Schiff base compounds (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have excellent pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). we report here, the crystal structure of the title new Schiff base compound, Fig. 1, derived from the condensation reaction of 2-hydroxy-4-methoxybenzaldehyde with isonicotinohydrazide is reported. The molecular structure of the title compound displays a trans configuration with respect to the C═N and C–N bonds. There is an intramolecular O—H···N hydrogen bond in the molecule. The dihedral angle between the benzene ring and the pyridine ring is 27.3 (2)°. All the bond lengths are within normal ranges and comparable to those in other similar compounds (Mohd Lair et al., 2009; Fun et al., 2008; Yang, 2008; Zhi, 2008; Zhi & Yang, 2007; Zhi, 2009). In the crystal, molecules are linked by interactions N—H···N into zigzag chains with graph-set notation C(7) along [010] (Bernstein, et al., 1995 ). An intramolecular O—H···N hydrogen bond is observed. (Table 1 and Fig. 2).

Experimental

2-Hydroxy-4-methoxybenzaldehyde (0.01 mol, 1.52 g) and isonicotinohydrazide (0.01 mol, 1.37 g) were dissolved in a methanol solution (50 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent for a week at room temperature.