(E)-N′-(5-Bromo-2-methoxy­benzyl­idene)-4-methoxy­benzohydrazide

Hong-Yan Ban; Cong-Ming Li

doi:10.1107/S1600536808035472

. 2008 Nov 8;64(Pt 12):o2260. doi: 10.1107/S1600536808035472

(E)-N′-(5-Bromo-2-methoxybenzylidene)-4-methoxybenzohydrazide

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

PMCID: PMC2959874 PMID: 21581241

Abstract

In the title compound, C₁₆H₁₅BrN₂O₃, the benzohydrazide group is not planar and the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 75.6 (2)°. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds involving carbonyl and amine functionalities, to form chains parallel to the c cell axis.

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: Yehye et al. (2008 ▶); Fun, Patil, Jebas et al. (2008 ▶); Fun, Patil, Rao et al. (2008 ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₅BrN₂O₃
M _r = 363.21
Monoclinic,
a = 12.438 (4) Å
b = 16.684 (6) Å
c = 7.863 (3) Å
β = 108.218 (6)°
V = 1549.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.67 mm⁻¹
T = 298 (2) K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.593, T _max = 0.620
8697 measured reflections
3245 independent reflections
2068 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.093
S = 1.01
3245 reflections
205 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.47 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 global, I. DOI: 10.1107/S1600536808035472/bh2202sup1.cif

e-64-o2260-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035472/bh2202Isup2.hkl

e-64-o2260-Isup2.hkl^{(159.2KB, 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	0.890 (10)	1.966 (12)	2.835 (3)	165 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support of this work was provided by the Research Foundation of Liaoning Province (project 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, Patil, Jebas et al., 2008; Fun, Patil, Rao et al., 2008;Yang et al., 2008; Ejsmont et al., 2008). We report herein the crystal structure of the title new compound, (I).

In the structure of the title compound (Fig. 1) the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 75.6 (2)°. In both the 5-bromo-2-methoxyphenyl unit and the 4-methoxyphenyl unit, the methoxy groups are nearly coplanar with the corresponding mean planes of the C1···C6 and C9···C14 rings, respectively. Atoms C16 and C15 deviate from their corresponding benzene rings by 0.058 (2) and 0.059 (2) Å respectively. The torsion angle of C7—N1—N2—C8 is 19.4 (3)°. The bond lengths and angles are found in expected ranges.

In the crystal structure, molecules are linked by intermolecular N—H···O hydrogen bonds involving carbonyl and amine groups (Table 1), to form chains parallel to the c axis (Fig. 2).

Experimental

The compound was prepared by refluxing 5-bromo-2-methoxybenzaldehyde (1.0 mmol) with 4-methoxybenzohydrazide (1.0 mmol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colorless solid product was filtered, and washed three times with methanol. Colorless block crystals of the title compound were obtained from a methanol solution by slow evaporation in air.