N′-(5-Bromo-2-hydr­oxy-3-methoxy­benzyl­idene)isonicotinohydrazide

San-Jun Peng; Hai-Yun Hou

doi:10.1107/S1600536808029607

. 2008 Sep 24;64(Pt 10):o1995. doi: 10.1107/S1600536808029607

N′-(5-Bromo-2-hydroxy-3-methoxybenzylidene)isonicotinohydrazide

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

PMCID: PMC2959402 PMID: 21201194

Abstract

The title compound, C₁₄H₁₂BrN₃O₃, was prepared by reaction of 5-bromo-3-methoxysalicylaldehyde and isonicotinohydrazide in methanol. The molecule is not planar and adopts a trans configuration with respect to the C=N bond. There is an intramolecular O—H⋯N hydrogen bond in the molecule. The dihedral angle between the benzene and pyridine rings is 12.2 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯N hydrogen bonds, forming chains running along the c-axis direction.

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

C₁₄H₁₂BrN₃O₃
M _r = 350.18
Monoclinic,
a = 7.4937 (9) Å
b = 15.8843 (19) Å
c = 11.7994 (14) Å
β = 99.776 (2)°
V = 1384.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.98 mm⁻¹
T = 298 (2) K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.587, T _max = 0.616 (expected range = 0.557–0.584)
8003 measured reflections
3013 independent reflections
2299 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.076
S = 1.03
3013 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.41 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/S1600536808029607/sj2539sup1.cif

e-64-o1995-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029607/sj2539Isup2.hkl

e-64-o1995-Isup2.hkl^{(147.9KB, 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	0.889 (10)	2.255 (13)	3.126 (3)	166 (3)
O1—H1⋯N1	0.82	1.93	2.643 (2)	145

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Symmetry code: (i) Inline graphic .

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 continuation of our work in this area (Peng & Hou, 2008) we report here the crystal structure of the title compound, (I), Fig. 1.

In the molecule of the title compound (I) the C7═N1 length of 1.275 (3) Å indicates a typical C═N bond. The molecule exists in a trans configuration with respect to the methylidene unit (C7═N1), as observed in other similar compounds (Han et al., 2006; Lu et al., 2008). There is an intramolecular O—H···N hydrogen bond in the molecule. The dihedral angle between the benzene and pyridine rings is 12.2 (2)°, indicating the molecule is not planar. The bond lengths are in normal ranges (Allen et al., 1987).

In the crystal structure, molecules are linked through intermolecular N—H···N hydrogen bonds (Table 1), forming chains running along the c direction (Fig. 2).

Experimental

5-Bromo-3-methoxysalicylaldehyde (0.231 g, 1 mmol) was dissolved in methanol (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 an absolute methanol yielded block-like single crystals of the compound.