(E)-4-Bromo-N′-(2-hydr­oxy-1-naphthyl­methyl­ene)benzohydrazide

Yun-Peng Diao; Qi-Hui Zhang; Da-Cheng Wang; Xu-Ming Deng

doi:10.1107/S1600536808031395

. 2008 Oct 4;64(Pt 11):o2070. doi: 10.1107/S1600536808031395

(E)-4-Bromo-N′-(2-hydroxy-1-naphthylmethylene)benzohydrazide

Yun-Peng Diao ^a,^b, Qi-Hui Zhang ^c, Da-Cheng Wang ^a, Xu-Ming Deng ^a,^*

PMCID: PMC2959633 PMID: 21580936

Abstract

The title compound, C₁₈H₁₃BrN₂O₂, was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 4-bromobenzohydrazide. This Schiff base molecule has an E configuration about the C=N bond and is almost planar, the dihedral angle between the mean planes through the substituted benzene ring and the naphthyl system being 6.6 (2)°. There is an intramolecular O—H⋯N hydrogen bond involving the naphthyl hydroxy substituent and the N′ atom of the hydrazide group. In the crystal structure, molecules are linked through intermolecular N—-H⋯O hydrogen bonds to form chains extending along the b direction.

Related literature

For related structures, see: Brückner et al. (2000 ▶); Diao (2007 ▶); Diao et al. (2007 ▶, 2008 ▶); Harrop et al. (2003 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C₁₈H₁₃BrN₂O₂
M _r = 369.21
Monoclinic,
a = 6.185 (2) Å
b = 4.7638 (19) Å
c = 25.689 (10) Å
β = 95.449 (7)°
V = 753.5 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.74 mm⁻¹
T = 298 (2) K
0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.494, T _max = 0.514 (expected range = 0.446–0.464)
5817 measured reflections
3119 independent reflections
2443 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.101
S = 0.90
3119 reflections
212 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), 1493 Friedel pairs
Flack parameter: 0.026 (12)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536808031395/su2066sup1.cif

e-64-o2070-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031395/su2066Isup2.hkl

e-64-o2070-Isup2.hkl^{(153KB, 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—H1⋯O1ⁱ	0.89 (3)	1.99 (3)	2.841 (4)	160 (6)
O2—H2⋯N2	0.82	1.86	2.580 (4)	145

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Schiff base compounds have been found to have potential pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). Recently, a few Schiff base compounds obtained from the reaction of aldehydes with benzohydrazides have been reported (Diao et al., 2008; Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007). As a further study of such compounds, we report here on the structure of the title compound.

The title compound, a Schiff base synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 4-bromobenzohydrazide, is almost planar (Fig. 1), with the dihedral angle between the mean planes of the substituted benzene ring and the naphthyl ring being only 6.6 (2)°. The torsion angles C4—C6—N1—N2 and C8—C7—N2—N1 are 0.9 (3) and 2.9 (3)°, respectively. There is an intramolecular O-H···N hydrogen bond involving the naphthyl hydroxyl substituent and the NH H-atom of the hydrazide group (Table 1).

In the crystal molecules are linked via N–H···O intermolecular hydrogen bonds (Table 1), to form chains extending in the b direction (Fig. 2).

Experimental

4-Bromobenzaldehyde (0.1 mmol, 18.5 mg) and 2-hydroxy-1-naphthaldehyde (0.1 mmol, 17.2 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 1 h and cooled to room temperature. After keeping the solution in air for alomost two weeks, yellow block-like crystals of the title compound were formed.