N′-(5-Bromo-2-methoxy­benzyl­idene)-4-hydroxy­benzohydrazide methanol solvate

Xue-Song Lin; Ya-Li Sang

doi:10.1107/S1600536809022983

. 2009 Jun 20;65(Pt 7):o1650. doi: 10.1107/S1600536809022983

N′-(5-Bromo-2-methoxybenzylidene)-4-hydroxybenzohydrazide methanol solvate

Xue-Song Lin ^a,^*, Ya-Li Sang ^a

PMCID: PMC2969367 PMID: 21582914

Abstract

In the title hydrazone compound, C₁₅H₁₃BrN₂O₃·CH₃OH, the methanol solvate is linked to the benzohydrazide molecule through O—H⋯N and O—H⋯O hydrogen bonds. The benzohydrazide molecule adopts an E configuration about the C=N double bond. The molecule is twisted, with a dihedral angle between the two substituted benzene rings of 35.7 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming layers parallel to the ac plane.

Related literature

For the biological properties of the hydrazone compounds, see: Khattab (2005 ▶); Küçükgüzel et al. (2003 ▶); Çukurovalı et al. (2006 ▶). For the structures of hydrazone derivatives, see: Fun et al. (2008 ▶); Wei et al. (2009 ▶); Khaledi et al. (2008 ▶); Yang et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₃·CH₄O
M _r = 381.23
Orthorhombic,
a = 11.1886 (7) Å
b = 14.4464 (9) Å
c = 20.5927 (13) Å
V = 3328.5 (4) Å³
Z = 8
Mo Kα radiation
μ = 2.49 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.598, T _max = 0.636
19306 measured reflections
3638 independent reflections
2234 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.179
S = 1.06
3638 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.83 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022983/at2817sup1.cif

e-65-o1650-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022983/at2817Isup2.hkl

e-65-o1650-Isup2.hkl^{(178.5KB, 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
N2—H2⋯O3ⁱ	0.89 (4)	2.16 (5)	3.009 (4)	158 (5)
O4—H4⋯N1	0.82	2.64	3.239 (5)	131
O4—H4⋯O2	0.82	1.96	2.729 (4)	157
O3—H3⋯O4ⁱⁱ	0.82	1.78	2.602 (5)	175

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

Acknowledgments

We are gratefully acknowledge Chifeng University for research funding.

supplementary crystallographic information

Comment

Hydrazone and Schiff base compounds derived from the reaction of aldehydes with hydrazides have been widely investigated both for their crystal structures and biological properties (Khattab et al., 2005; Küçükgüzel et al., 2003; Çukurovalı et al., 2006). In the last few years, a large number of hydrazone derivatives have been reported (Fun et al., 2008; Wei et al., 2009; Khaledi et al., 2008; Yang et al., 2008). However, the hydrazone compounds derived the 5-bromo-2-methoxybenzaldehyde have never been reported. In this paper, the crystal structure of the title new hydrazone compound, (I), derived from the reaction of 5-bromo-2-methoxybenzaldehyde and 4-hydroxybenzohydrazide, is reported.

The molecular structure of (I) is shown as Fig. 1. The compound consists of a hydrazone molecule and a methanol molecule of crystallization. The methanol molecule is linked to the hydrazone molecule through intramolecular O–H···N and O–H···O hydrogen bonds, Table 1. The hydrazone molecule adopts an E configuration about the C═N double bond. The molecule is twisted, with the dihedral angle between the C1—C6 and C10—C15 benzene rings of 35.7 (2)°. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds, Table 1, forming layers parallel to the ac plane, as shown in Fig. 2.

Experimental

5-Bromo-2-methoxybenzaldehyde (1.0 mmol, 215.0 mg) and 4-hydroxybenzohydrazide (1.0 mmol, 152.2 mg) were mixed and refluxed in methanol (50 ml). The mixture was stirred for 1 h to give a clear colourless solution. Colourless crystals of (I) were formed by slow evaporation of the solution in air for a few days.