N′-(5-Bromo-2-methoxy­benzyl­idene)-3,4-methyl­enedioxy­benzohydrazide

Ya-Li Sang; Xue-Song Lin

doi:10.1107/S1600536809022818

. 2009 Jun 20;65(Pt 7):o1636. doi: 10.1107/S1600536809022818

N′-(5-Bromo-2-methoxybenzylidene)-3,4-methylenedioxybenzohydrazide

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

PMCID: PMC2969257 PMID: 21582901

Abstract

In the title molecule, C₁₆H₁₃BrN₂O₄, the two benzene rings form a dihedral angle of 74.9 (2)°. In the crystal, molecules are linked via intermolecular N—H⋯O hydrogen bonds into chains propagating along the c axis.

Related literature

For the biological activity of hydrazone derivatives, see: Khattab (2005 ▶); Küçükgüzel et al. (2003 ▶); Cukurovali et al. (2006 ▶). For the crystal structures of related compounds, see: Fun et al. (2008 ▶); Wei et al. (2009 ▶); Khaledi et al. (2008 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₃BrN₂O₄
M _r = 377.19
Monoclinic,
a = 12.678 (1) Å
b = 16.217 (2) Å
c = 7.846 (2) Å
β = 104.804 (3)°
V = 1559.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.66 mm⁻¹
T = 298 K
0.30 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.503, T _max = 0.534 (expected range = 0.460–0.488)
8368 measured reflections
3110 independent reflections
1932 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.096
S = 1.04
3110 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.47 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/S1600536809022818/cv2572sup1.cif

e-65-o1636-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022818/cv2572Isup2.hkl

e-65-o1636-Isup2.hkl^{(152.6KB, 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
N2—H2⋯O2ⁱ	0.89 (3)	1.96 (3)	2.841 (3)	168 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We gratefullly acknowledge Chifeng University for the funding of this study.

supplementary crystallographic information

Comment

Hydrazone compounds have been widely investigated due to their interesting biological properties, such as antibacterial and antitumor activities (Khattab, 2005; Küçükgüzel et al., 2003; Cukurovali et al., 2006). Recently, a number of crystal structures 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 title new hydrazone compound is reported.

The molecular structure of the title compound is shown inFig. 1. The molecule adopts an E configuration with respect to the C═N bond. The dihedral angle between the two substituted benzene rings is 74.9 (2)°.

In the crystal, the molecules are linked via intermolecular N—H···O hydrogen bonds (Table 1) into chains propagated along c axis.

Experimental

3,4-(Methylenedioxy)benzohydrazide (1.0 mmol, 180.2 mg) and 5-bromo-2-methoxybenzaldehyde (1.0 mmol, 215.0 mg) were mixed and refluxed in ethanol (50 ml). The mixture was stirred for 1 h to give a clear colorless solution. Colourless crystals of the title compound were formed by slow evaporation of the solution in air.