(E)-3-Bromo-N′-(2-hydr­oxy-1-naphthyl­idene)benzohydrazide

Guo-Biao Cao; Xu-Hui Lu

doi:10.1107/S1600536809022533

. 2009 Jun 17;65(Pt 7):o1600. doi: 10.1107/S1600536809022533

(E)-3-Bromo-N′-(2-hydroxy-1-naphthylidene)benzohydrazide

Guo-Biao Cao ^a,^*, Xu-Hui Lu ^a

PMCID: PMC2969212 PMID: 21582874

Abstract

The title compound, C₁₈H₁₃BrN₂O₂, was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The dihedral angle between the benzene ring and the naphthyl ring system is 18.3 (2)°. An intramolecular O—H⋯N hydrogen bond is observed between the phenolate O and imine N atoms. In the crystal structure, molecules are linked through intermolecular N—H⋯O and C—H⋯O hydrogen bonds, forming a chain running along [101].

Related literature

For crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Li & Ban (2009 ▶); Zhu et al. (2009 ▶); Yang (2007 ▶); You et al. (2008 ▶). For hydrazone compounds reported previously by our group, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C₁₈H₁₃BrN₂O₂
M _r = 369.21
Monoclinic,
a = 7.257 (1) Å
b = 31.229 (2) Å
c = 7.327 (1) Å
β = 109.186 (2)°
V = 1568.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.63 mm⁻¹
T = 298 K
0.27 × 0.24 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.505, T _max = 0.548
9563 measured reflections
3393 independent reflections
2177 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.130
S = 1.03
3393 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536809022533/rz2335sup1.cif

e-65-o1600-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022533/rz2335Isup2.hkl

e-65-o1600-Isup2.hkl^{(166.4KB, 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	1.86	2.584 (4)	146
N2—H2⋯O2ⁱ	0.90 (3)	1.99 (2)	2.840 (4)	159 (4)
C11—H11⋯O2ⁱ	0.92	2.42	3.138 (4)	134

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Symmetry code: (i) Inline graphic .

Acknowledgments

The Vital Foundation of Ankang University (project No. 2008AKXY012) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02JK202) are gratefully acknowledged.

supplementary crystallographic information

Comment

Study on the crystal structures of hydrazone derivatives is a hot topic in structural chemistry. In the last few years, the crystal structures of a large number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008), the title new hydrazone compound derived from the reaction of 2-hydroxynaphthaldehyde with an equimolar quantity of 3-bromobenzohydrazide is reported.

In the title compound compound (Fig. 1), the dihedral angle between the benzene ring system and the naphthyl ring is 18.3 (2)°. An intramolecular O—H···N hydrogen bond is observed between the phenolate O and imine N atoms. In the crystal structure, molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) to form a chain running along [101] (Fig. 2).

Experimental

The title compound was prepared by refluxing equimolar quantities of 2-hydroxynaphthaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed by slow evaporation of the solution in air.