N′-(3-Bromo-4-methoxy­benzyl­idene)nicotinohydrazide monohydrate

Feng-Yu Bao; Xing-Shun Ding; Hai-Yan Zhang; Ying-Xia Zhou

doi:10.1107/S160053680903400X

. 2009 Aug 29;65(Pt 9):o2282. doi: 10.1107/S160053680903400X

N′-(3-Bromo-4-methoxybenzylidene)nicotinohydrazide monohydrate

Feng-Yu Bao ^a,^*, Xing-Shun Ding ^b, Hai-Yan Zhang ^a, Ying-Xia Zhou ^a

PMCID: PMC2969945 PMID: 21577675

Abstract

In the title compound, C₁₄H₁₂BrN₃O₂·H₂O, the benzene ring is oriented at a dihedral angle of 39.66 (11)° with respect to the pyridine ring. The solvent water molecule links with the organic compound via O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonding.

Related literature

For applications of Schiff base compounds, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶).

Experimental

Crystal data

C₁₄H₁₂BrN₃O₂·H₂O
M _r = 352.18
Monoclinic,
a = 7.7979 (1) Å
b = 12.5678 (2) Å
c = 14.9419 (3) Å
β = 97.449 (1)°
V = 1451.98 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.85 mm⁻¹
T = 296 K
0.43 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.400, T _max = 0.535
12611 measured reflections
3149 independent reflections
2525 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.069
S = 1.01
3149 reflections
198 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S160053680903400X/xu2597sup1.cif

e-65-o2282-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903400X/xu2597Isup2.hkl

e-65-o2282-Isup2.hkl^{(154.5KB, 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
O2—H2A⋯N3	0.85 (2)	2.05 (2)	2.886 (2)	168 (2)
O2—H2B⋯O1ⁱ	0.82 (3)	2.47 (3)	3.118 (2)	136 (2)
O2—H2B⋯N1ⁱ	0.82 (3)	2.43 (3)	3.197 (2)	156 (3)
N2—H2⋯O2ⁱⁱ	0.86	2.18	2.982 (2)	155

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

supplementary crystallographic information

Comment

The chemistry of Schiff bases has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of our interest in the coordination chemistry of Schiff bases, we have recently synthesized the title compound and report here its crystal structure.

The title molecule crystallizes in the E conformation, with the C8—N1—N2—C9 torsion angle of 170.02 (19)°. The molecular is non-planar, there is a dihedral angle of 39.66 (11)° between the benzene ring and the pyridine ring. In the crystal structure, the lattice water molecule links with the organic compound via O—H···O, O—H···N and N—H···O hydrogen bonding.

Experimental

Nicotinohydrazide (1 mmol, 0.137 g) was dissolved in ethanol (15 ml). The mixture was stirred for several min at 351 K, then 3-bromo-4-methoxybenzaldehyde (1 mmol, 0.215 g) in ethanol (8 mm l) was added dropwise and the mixture was refluxed for 2 h. The solid product was isolated and recrystallized from methanol, colourless single crystals were obtained after 3 d.