N′-(3,5-Dibromo-2-hydroxy­benzyl­idene)-3,4-methyl­enedioxy­benzohydrazide

Ya-Li Sang; Xue-Song Lin

doi:10.1107/S160053680902282X

. 2009 Jun 20;65(Pt 7):o1631–o1632. doi: 10.1107/S160053680902282X

N′-(3,5-Dibromo-2-hydroxybenzylidene)-3,4-methylenedioxybenzohydrazide

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

PMCID: PMC2969430 PMID: 21582898

Abstract

In the asymmetric unit of the title hydrazone compound, C₁₅H₁₀Br₂N₂O₄, there are two independent molecules. In each molecule, the five-membered ring adopts a flattened envelope conformation; the flap atoms are displaced by 0.114 (2) and 0.219 (2) Å from the planes of the other four atoms. In one molecule the dihedral angle between the two benzene rings is 22.8 (2)°, while in the other it is 40.8 (2)°. Each molecule displays an E configuration with respect to the C=N bond. In both molecules, intramolecular O—H⋯N hydrogen bonds are observed. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological properties of hydrazones, see: Khattab et al. (2005 ▶); Küçükgüzel et al. (2003 ▶); Cukurovali et al. (2006 ▶). For their coordination chemistry, see: Iskander et al. (2001 ▶); Bernhardt et al. (2004 ▶); Aggarwal et al. (1981 ▶); Thomas et al. (1979 ▶). For the crystal structures of other reported hydrazones, 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

C₁₅H₁₀Br₂N₂O₄
M _r = 442.07
Triclinic,
a = 9.793 (1) Å
b = 13.188 (2) Å
c = 13.342 (2) Å
α = 76.282 (2)°
β = 78.350 (2)°
γ = 75.911 (2)°
V = 1604.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 5.07 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.388, T _max = 0.416 (expected range = 0.322–0.345)
9190 measured reflections
6633 independent reflections
4090 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.141
S = 0.98
6633 reflections
423 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.55 e Å⁻³
Δρ_min = −0.66 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/S160053680902282X/wn2332sup1.cif

e-65-o1631-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902282X/wn2332Isup2.hkl

e-65-o1631-Isup2.hkl^{(324.6KB, 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⋯N1	0.82	2.00	2.654 (4)	137
O5—H5⋯N3	0.82	1.86	2.582 (4)	146
N2—H2⋯O6ⁱ	0.91 (4)	1.99 (3)	2.833 (5)	155 (6)
N4—H4A⋯O2ⁱⁱ	0.90 (3)	2.04 (3)	2.888 (5)	158 (6)

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

Acknowledgments

We are very grateful to Chifeng University for research funding.

supplementary crystallographic information

Comment

Hydrazone compounds have been widely investigated due to their interesting biological properties, such as antibacterial and antitumor activities (Khattab et al., 2005; Küçükgüzel et al., 2003; Cukurovali et al., 2006). Furthermore, hydrazones are excellent ligands in coordination chemistry, forming a large number of metal complexes (Iskander et al., 2001; Bernhardt et al., 2004; Aggarwal et al., 1981; Thomas et al., 1979). Recently, the crystal structures of 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). In this paper, the crystal structure of the new title hydrazone compound is reported.

In the asymmetric unit there are two independent molecules (Fig. 1), which assume E configurations with respect to the C═N bonds. In each molecule the five-membered ring adopts a flattened envelope conformation; the flap atoms C15 and C30 are displaced by 0.114 (2) and 0.219 (2) Å, respectively, from the planes of the other four atoms. In one molecule the dihedral angle between the two benzene rings is 22.8 (2)°; in the other it is 40.8 (2)°. All bond lengths are within normal values (Allen et al., 1987). In both molecules, intramolecular O—H···N hydrogen bonds (Table 1) are observed. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis, as shown in Fig. 2.

Experimental

3,4-(Methylenedioxy)benzohydrazide (1.0 mmol, 180.2 mg) and 3,5-dibromo-2-hydroxybenzaldehyde (1.0 mmol, 280.0 mg) were mixed and refluxed in aqueous ethanol (95% ethanol : 5% water; 50 ml). The mixture was stirred for 1 h to give a clear colorless solution. Colorless crystals of the title compound were formed by slow evaporation of the solution in air.