(E)-N′-(5-Bromo-2-methoxy­benzyl­idene)-3-methoxy­benzohydrazide

Cong-Ming Li; Hong-Yan Ban

doi:10.1107/S1600536809010435

. 2009 Mar 28;65(Pt 4):o883. doi: 10.1107/S1600536809010435

(E)-N′-(5-Bromo-2-methoxybenzylidene)-3-methoxybenzohydrazide

Cong-Ming Li ^a,^*, Hong-Yan Ban ^b

PMCID: PMC2968868 PMID: 21582592

Abstract

In the title compound, C₁₆H₁₅BrN₂O₃, there are two independent molecules (A and B) in the asymmetric unit. The major difference between the two molecules is the dihedral angle formed by the aromatic rings [72.6 (2) and 18.8 (2)° for A and B, respectively]. The benzohydrazide groups are not planar and the molecules exist in trans configurations with respect to the methylidene units. The molecular packing is stabilized by two intermolecular N—H⋯O hydrogen bonds, forming chains parallel to the c axis. Only the A molecules of the asymmetric unit are held together by π–π interactions [centroid–centroid distance = 3.714 (3) Å].

Related literature

For the biological activities of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban & Li (2008a ▶,b ▶); Yehye et al. (2008 ▶); Fun et al. (2008a ▶,b ▶);Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₅BrN₂O₃
M _r = 363.21
Monoclinic,
a = 29.063 (3) Å
b = 10.934 (2) Å
c = 9.913 (2) Å
β = 96.77 (3)°
V = 3128.1 (9) Å³
Z = 8
Mo Kα radiation
μ = 2.64 mm⁻¹
T = 298 K
0.35 × 0.33 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.458, T _max = 0.505 (expected range = 0.411–0.453)
25535 measured reflections
6785 independent reflections
3586 reflections with I > 2σ(I)
R _int = 0.076

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.163
S = 1.03
6785 reflections
407 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536809010435/bx2199sup1.cif

e-65-0o883-sup1.cif^{(25.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010435/bx2199Isup2.hkl

e-65-0o883-Isup2.hkl^{(332.1KB, 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	0.90 (3)	2.03 (3)	2.872 (5)	155 (5)
N4—H4A⋯O5ⁱⁱ	0.90 (3)	2.04 (3)	2.868 (5)	153 (5)

Open in a new tab

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

Acknowledgments

Financial support of this work was provided by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Hydrazones derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of hydrazones have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported two hydrazones (Ban & Li, 2008a,b). In this paper, we report herein the crytal structure of the title new compound, (I).

In the structure of the title compound, Fig. 1, there are two independent molecules. Each molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angles between the two substituted benzene rings are 72.6 (2) and 18.8 (2)°, respectively. The torsion angles of C7-N1-N2-C8 and C22-N3-N4-C23 are 12.2 (3) and 4.6 (3)°, respectively. The molecular packing is stabilized by two intermolecular N-H···O hydrogen bond to form chains parallel to the c axis, Fig 2. Only the A molecules of the asymmetric unit are held together by π - π interactions [Cg···Cgi(-x+1, -y,-z+1) = 3.714 (3) Å; Cg is the centroid of the C1–C6 ring].

Experimental

The compound was prepared by refluxing 5-bromo-2-methoxybenzaldehyde (1.0 mol, 215.0 mg) with 3-methoxybenzohydrazide (1.0 mol, 166.2 mg) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colourless solid product was filtered, and washed three times with methanol. Colourless block crystals of the title compound were obtained from a methanol solution by slow evaporation in air.