N′-(2-Bromo­benzyl­idene)-3,4,5-tri­methoxy­benzohydrazide methanol solvate

Yong-Chuang Zhu; Dao-Hang He

doi:10.1107/S1600536808021764

. 2008 Jul 31;64(Pt 8):o1630. doi: 10.1107/S1600536808021764

N′-(2-Bromobenzylidene)-3,4,5-trimethoxybenzohydrazide methanol solvate

Yong-Chuang Zhu ^a, Dao-Hang He ^a,^*

PMCID: PMC2962239 PMID: 21203320

Abstract

The title compound, C₁₇H₁₇BrN₂O₄·CH₄O, was synthesized by the condensation of 3,4,5-trimethoxybenzohydrazide and 2-bromobenzaldehyde. The two aromatic rings are approximately planar, the dihedral angle being 3.08 (9)°. The molecules are linked by intermolecular N—H⋯O and O—H⋯O hydrogen bonds into chains along the a axis.

Related literature

For related literature, see: Constable & Holmes (1987 ▶); Ganjali et al. (2006 ▶); Gardner et al. (1991 ▶); Jing et al. (2006 ▶); Kuriakose et al. (2007 ▶); Patole et al. (2003 ▶); Zhou et al. (2005 ▶).

Experimental

Crystal data

C₁₇H₁₇BrN₂O₄·CH₄O
M _r = 425.28
Orthorhombic,
a = 12.9234 (7) Å
b = 4.9159 (3) Å
c = 29.3975 (17) Å
V = 1867.63 (19) Å³
Z = 4
Mo Kα radiation
μ = 2.23 mm⁻¹
T = 173 (2) K
0.36 × 0.35 × 0.33 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.455, T _max = 0.479
8158 measured reflections
3799 independent reflections
3206 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.080
S = 1.04
3799 reflections
240 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ▶), 1720 Friedel pairs
Flack parameter: −0.008 (8)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536808021764/wn2271sup1.cif

e-64-o1630-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021764/wn2271Isup2.hkl

e-64-o1630-Isup2.hkl^{(186.3KB, 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
N1—H1A⋯O5ⁱ	0.88	2.01	2.871 (4)	164
O5—H5⋯O4	0.84	1.96	2.794 (3)	175

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Natural Science Youth Foundation of South China University of Technology for financial assistance (E5050570).

supplementary crystallographic information

Comment

Hydrazones are acknowledged to possess a diverse range of bioactivities; these include antibacterial, antiviral, antineoplastic, and anti-inflammatory (Constable & Holmes, 1987; Ganjali et al., 2006; Gardner et al., 1991; Patole et al., 2003). In addition, many hydrazones have also been used as ligands because they can readily form stable complexes with most metal ions (Kuriakose et al., 2007; Zhou et al., 2005). We report here the synthesis and crystal structure of the title compound, obtained by the condensation of 3,4,5-trimethoxybenzohydrazide and 2-bromobenzaldehyde.

The asymmetric unit of the title compound comprises one N'-(2-bromobenzylidene)-3,4,5-trimethoxybenzohydrazide and a methanol solvent molecule (Fig. 1). The two aromatic rings are approximately planar, with a dihedral angle of 3.08 (9)°. Similar geometry has been observed in related hydrazone analogues (Jing et al., 2006). The methanol molecules in the crystal structure are linked to N'-(2-bromobenzylidene)-3,4,5-trimethoxybenzohydrazide through intermolecular N—H···O and O—H···O hydrogen bonds into chains along the a axis (Fig. 2).

Experimental

A mixture of 3,4,5-trimethoxybenzohydrazide (1 mmol) and 2-bromobenzaldehyde (1 mmol) in anhydrous ethanol (10 ml) was refluxed for 2 h. When the solution was cooled to room temperature, some white needles separated out. After filtration, colorless single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.