(E)-N′-(5-Bromo-2-hydroxy­benzyl­idene)-3,4,5-trimethoxy­benzohydrazide

Zhen-dong Zhao; Yu-min Wang; Yu-xiang Chen; Liang-wu Bi

doi:10.1107/S1600536808038464

. 2008 Nov 22;64(Pt 12):o2408. doi: 10.1107/S1600536808038464

(E)-N′-(5-Bromo-2-hydroxybenzylidene)-3,4,5-trimethoxybenzohydrazide

Zhen-dong Zhao ^a,^*, Yu-min Wang ^a, Yu-xiang Chen ^a, Liang-wu Bi ^a

PMCID: PMC2960056 PMID: 21581377

Abstract

The molecule of the title compound, C₁₇H₁₇BrN₂O₅, assumes an E configuration, with the 5-bromo-2-hydroxyphenyl and benzohydrazide units located on opposite sites of the C=N double bond. The dihedral angle between the planes of the two benzene rings is 32.48 (15)°. The crystal structure is stabilized by intramolecular O—H⋯N and intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Yang et al. (1996 ▶); Nawar & Hosny (2000 ▶); Pelagatti et al. (1999 ▶); Ainscough et al. (1998 ▶). For related structures, see: Diao & Yu (2006 ▶); Jing et al. (2005 ▶); Wang et al. (2008 ▶).

Experimental

Crystal data

C₁₇H₁₇BrN₂O₅
M _r = 409.24
Monoclinic,
a = 11.4157 (19) Å
b = 16.279 (3) Å
c = 9.3738 (16) Å
β = 100.210 (3)°
V = 1714.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.43 mm⁻¹
T = 273 (2) K [Unusual. Please check]
0.15 × 0.10 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.712, T _max = 0.868
8954 measured reflections
3037 independent reflections
2065 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.097
S = 1.01
3037 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 I, global. DOI: 10.1107/S1600536808038464/pv2120sup1.cif

e-64-o2408-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038464/pv2120Isup2.hkl

e-64-o2408-Isup2.hkl^{(149KB, 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⋯N2	0.82	1.92	2.642 (3)	145
N1—H1A⋯O2ⁱ	0.86	2.14	2.888 (3)	146

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Natural Science Foundation of China (grant No. 30571466).

supplementary crystallographic information

Comment

Salicyladelhyde hydrazones have received considerable attention because of their possible applications in catalysis and pharmacology (Yang et al., 1996; Nawar & Hosny, 2000; Pelagatti et al., 1999; Ainscough et al., 1998). As part of our ongoing investigation on acylhydrazone compounds (Wang et al., 2008) and their metal complexes, we have obtained the title compound, (I), from a condensation of 3,4,5-trimethoxybenzohydrazide and 5-bromo-2-hydroxybenzaldehyde, and report its crystal structure in this paper.

The molecular structure of (I) (Fig. 1) contains 3,4,5-trimethoxybenzohydrazide and 5-bromo-2-hydroxybenzaldehyde moities that are located on opposite sides of the C═N double bond exhibiting an E configuration about C═N. The dihedral angle between the mean-planes of the two benzene rings is 32.48 (15)°. The crystal structure involves an intramolecular hydrogen bond O1–H1···N2, and is further stabilized by an intermolecular hydrogen bonds N1–H1A···O2, resulting in chains of molecules extended along the c-axis; details are given in Table 1 and Fig. 2. The bond distances and bond angles in (I) are in agreement with the corresponding dimensions reported for some structures closely related to (I) (Diao & Yu, 2006; Jing et al., 2005; Wang et al., 2008). (

Experimental

An ethanol solution (50 ml) of 3,4,5-trimethoxybenzohydrazide (0.01 mol) and 5-bromo-2-hydroxybenzaldehyde (0.01 mol) was refluxed and stirred for 2h ; the mixture was cooled and the resulting solid product, (I), was collected by filtration. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in THF.